5-Fluoro-1,3-thiazol-2-amine → (R)-5-chloro-N1-(5-fluorothiazol-2-yl)-N1'-methylspiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxamide

HRID 1411283Notes

Reaction equation

HRID 1411283 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C@:10]3([CH2:14][CH2:13][NH:12][CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20](Cl)=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1.ClC1C=C2C3(CCNC3)C[N:31]([C:38](NC3SC(Cl)=CN=3)=[O:39])[C:28]2=CC=1.NC1SC([F:53])=CN=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C@@:10]3([CH2:14][CH2:13][N:12]([C:38]([NH:31][CH3:28])=[O:39])[CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([F:53])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 100803855-Fluoro-1,3-thiazol-2-amineHCID 904492715-chloro-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamideHCID 90449948(S)-5-chloro-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide

Product 1

HCID 90449367(R)-5-chloro-N1-(5-fluorothiazol-2-yl)-N1'-methylspiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxamide

Procedure

The captioned compound was obtained in the form of a white solid by performing the same reactions and/or treatments as those in Example 373, with the exceptions that the (S)-5-chloro-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide obtained as an intermediate of Example 52 was used instead of 5-chloro-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide, and that 2-amino-5-fluorothiazole 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-4cdef9e51ea34df1a8519d2f46ef2a42
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

Loading…