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

HRID 1411273Notes

Reaction equation

HRID 1411273 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C@:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18](C)(C)C)=[O:16])[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1.Cl.[NH2:23][C:24]1[S:25][C:26]([F:29])=[CH:27][N:28]=1.Cl[C:31](OC)=[O:32]>>[Br:1][C:2]1[CH:3]=[C:4]2[C@:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:31](=[O:32])[NH:23][C:24]3[S:25][C:26]([F:29])=[CH:27][N:28]=3)[C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 118589315-Fluoro-1,3-thiazol-2-amine hydrochlorideHCID 90449881(R)-t-butyl 5-bromospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Product 1

HCID 90449714(R)-methyl 5-bromo-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 (R)-t-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate was used instead of t-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, that 2-amino-5-fluorothiazole hydrochloride was used instead of 2-amino-5-chlorothiazole hydrochloride, and that methyl chloroformate was used instead of acetyl chloride.

Workup

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

Sources & evidence

ORD record
ord-170f33281ebb453cb6c686a2af97b8fe
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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