Methyl chloroformate → Methyl 5-chloro-1-((5-methylthiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 1411252Notes

Reaction equation

[Cl: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.[NH2:22][C:23]1[S:24][C:25]([CH3:28])=[CH:26][N:27]=1.Cl[C:30](OC)=[O:31]>>[Cl: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:30](=[O:31])[NH:22][C:23]3[S:24][C:25]([CH3:28])=[CH:26][N:27]=3)[C:5]2=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 6586Methyl chloroformate

HCID 3517702-Amino-5-methylthiazole

HCID 69813251Tert-butyl 5-chlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Product 1

HCID 90449385Methyl 5-chloro-1-((5-methylthiazol-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 t-butyl 5-chlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate was used instead of t-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, that 2-amino-5-methylthiazole was used instead of 2-amino-5-chlorothiazole hydrochloride, and that methyl chloroformate was used instead of acetyl chloride.

Workup

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

Sources & evidence

ORD record: ord-3b5ba34a5c0940f39e30a20470b08a50
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921576B2

Reaction notes

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