Methyl chloroformate → (S)-methyl 5,6-dichloro-1-((5-fluorothiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 1411272Notes

Reaction equation

HRID 1411272 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C@@:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19](C)(C)C)=[O:17])[CH2:12]3)[CH2:10][NH:9][C:5]2=[CH:6][C:7]=1[Cl:8].ClC([O:26][CH3:27])=O.Cl.[NH2:29][C:30]1[S:31][C:32]([F:35])=[CH:33][N:34]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C@@:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:27](=[O:26])[NH:29][C:30]3[S:31][C:32]([F:35])=[CH:33][N:34]=3)[C:5]2=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 118589315-Fluoro-1,3-thiazol-2-amine hydrochlorideHCID 90449743(S)-t-butyl 5,6-dichlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Product 1

HCID 90449941(S)-methyl 5,6-dichloro-1-((5-fluorothiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Procedure

The captioned compound was obtained in the form of a white solid by performing the same reactions and/or treatments as those in Examples 1, 2, and 3, with the exceptions that (S)-t-butyl 5,6-dichlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate was used instead of t-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, that methyl chloroformate was used instead of acetyl chloride, and that 2-amino-5-fluorothiazole hydrochloride was used instead of 2-amino-5-chlorothiazole hydrochloride.

Workup

  1. customThe captioned compound was obtained in the form of a white solid

Sources & evidence

ORD record
ord-93c0be87c35d46068193896e34b12a23
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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