Cyanoacetic acid → 5-chloro-N-(5-chlorothiazol-2-yl)-1'-(2-cyanoacetyl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide

HRID 1411249Notes

Reaction equation

HRID 1411249 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:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1.BrC1C=C2C3(CCNC3)CN(C(NC3SC(Cl)=CN=3)=O)C2=CC=1.[C:47]([CH2:49][C:50](O)=[O:51])#[N:48]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:50](=[O:51])[CH2:49][C:47]#[N:48])[CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 9740Cyanoacetic acidHCID 71522964HCID 71522964, compoundHCID 904492715-chloro-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide

Product 1

HCID 895207925-chloro-N-(5-chlorothiazol-2-yl)-1'-(2-cyanoacetyl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide

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 23, with the exceptions that the 5-chloro-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide obtained as an intermediate of Example 39 was used instead of 5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide, and that cyanoacetic acid was used instead of formic acid.

Workup

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

Sources & evidence

ORD record
ord-1a30dbd181cd4e47ac6d32878d258187
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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