Ethoxalyl chloride → N-(5-Chlorothiazol-2-yl)-1'-(2-(methylamino)-2-oxoacetyl)-5-(trifluoromethyl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide

HRID 1411282Notes

Reaction equation

HRID 1411282 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]3)[CH2:10][NH:9][C:6]2=[CH:7][CH:8]=1.Cl[C:26](=[O:32])[C:27]([O:29]CC)=O.Cl.[NH2:34][C:35]1[S:36][C:37]([Cl:40])=[CH:38][N:39]=1.[CH3:41][NH2:42].[O:43]1[CH2:47]CCC1>>[Cl:40][C:37]1[S:36][C:35]([NH:34][C:47]([N:9]2[C:6]3[C:5](=[CH:4][C:3]([C:2]([F:1])([F:24])[F:23])=[CH:8][CH:7]=3)[C:11]3([CH2:15][CH2:14][N:13]([C:27](=[O:29])[C:26]([NH:42][CH3:41])=[O:32])[CH2:12]3)[CH2:10]2)=[O:43])=[N:39][CH:38]=1

Participants

5

Reactant 4

HCID 20884Ethoxalyl chlorideHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 66615946Methylamine tetrahydrofuranHCID 90449647tert-Butyl 5-(trifluoromethyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Product 1

HCID 90449812N-(5-Chlorothiazol-2-yl)-1'-(2-(methylamino)-2-oxoacetyl)-5-(trifluoromethyl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide

Procedure

(tert-Butyl 5-(trifluoromethyl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, ethyl chloroglyoxylate, 2-amino-5-chlorothiazole hydrochloride, and a solution of methylamine-tetrahydrofuran)

Sources & evidence

ORD record
ord-5625264f09774624a0846f044b800709
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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