CAS 1208007-67-3

tert-Butyl 2(S)-(5-bromo-2-benzimidazolyl)pyrrolidine-1-carboxylate

Codes: Emitasvir Phosphate-003, RAVI-015

Application context (from source-drug indications)

Hepatitis CEmitasvir PhosphateRenal impairmentEmitasvir PhosphateHepatic function declineEmitasvir PhosphateChronic hepatitis CEmitasvir PhosphateHepatitis CRavidasvir HydrochlorideViral infectionRavidasvir HydrochlorideChronic hepatitis CRavidasvir Hydrochloride

Source drugs (routes using this intermediate)

Drug	Tier	Expiry
Emitasvir Phosphate	Tier C — Watch / trade	-
Ravidasvir Hydrochloride	Tier C — Watch / trade	-

Position in synthesis routes (up/downstream chain)

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Emitasvir PhosphateOptimised routesteps: 6total yield: 230.40mg(Emitasvir Phosphate (API))

2-Amino-4-bromophenylamine→N-Boc-L-proline→tert-Butyl 2(S)-(5-bromo-2-benzimidazolyl)pyrrolidine-1-carboxylate→tert-Butyl (2S)-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]pyrrolidine-1-carboxylate→tert-Butyl (2S)-2-[4-(4-[(1S,4R)-8-[(trifluoromethanesulfonyl)oxy]-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]phenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate→tert-Butyl (2S)-2-(4-[4-[(1S,4R)-8-[2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1H-benzimidazol-5-yl]-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]phenyl]-1H-imidazol-2-yl)pyrrolidine-1-carboxyla te→2-[(2S)-Pyrrolidin-2-yl]-5-[(1R,4S)-8-(4-[2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-4-yl]phenyl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-benzimidazole→2-[(2S)-Pyrrolidin-2-yl]-5-[(1R,4S)-8-(4-[2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-benzimidazole tetrahydrogen chloride→N-(Methoxycarbonyl)-L-valine→Methyl [(2S)-1-[(2S)-2-[5-[(1R,4S)-8-(4-[2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-4-yl]phenyl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-benzimi dazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

Ravidasvir HydrochlorideOriginator routesteps: 12total yield: 0.039 g

6-bromo-2-naphthoic acid→RAVI-002→RAVI-003→RAVI-004→(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid→RAVI-006→RAVI-007→RAVI-008→(methoxycarbonyl)-D-valine→RAVI-010→4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)→RAVI-012→RAVI-013→4-bromobenzene-1,2-diamine→RAVI-015→RAVI-016

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