Acetoxyacetyl chloride → 5-(3-(azetidin-1-yl)-3-oxopropyl)-1'-(2-hydroxyacetyl)-N-(5-methoxythiazol-2-yl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide

HRID 1411301Notes

Reaction equation

HRID 1411301 reaction equation
C(O[C:4](=[O:36])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:15]3([CH2:19][CH2:18][N:17]([C:20]([O:22]C(C)(C)C)=O)[CH2:16]3)[CH2:14][N:13]([C:27](OCC[Si](C)(C)C)=[O:28])[C:10]2=[CH:11][CH:12]=1)C.[NH2:37][C:38]1[S:39][C:40]([O:43][CH3:44])=[CH:41][N:42]=1.C(OC[C:50](Cl)=[O:51])(=O)C.Cl.[NH:54]1[CH2:57][CH2:56][CH2:55]1>>[N:54]1([C:4](=[O:36])[CH2:5][CH2:6][C:7]2[CH:8]=[C:9]3[C:15]4([CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH2:50][OH:51])[CH2:16]4)[CH2:14][N:13]([C:27]([NH:37][C:38]4[S:39][C:40]([O:43][CH3:44])=[CH:41][N:42]=4)=[O:28])[C:10]3=[CH:11][CH:12]=2)[CH2:57][CH2:56][CH2:55]1

Participants

5

Reactant 4

HCID 26297Acetoxyacetyl chlorideHCID 12308726Azetidine hydrochlorideHCID 203162835-Methoxy-1,3-thiazol-2-amineHCID 904497641-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(3-ethoxy-3-oxopropyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

Product 1

HCID 895205155-(3-(azetidin-1-yl)-3-oxopropyl)-1'-(2-hydroxyacetyl)-N-(5-methoxythiazol-2-yl)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 Step 5 of Example 383, and Examples 1, 2, 3, 29, and 85, with the exceptions that the 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(3-ethoxy-3-oxopropyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate obtained in Step 1 of Example 412 was used instead of 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate, that 2-amino-5-methoxythiazole was used instead of 2-amino-5-chlorothiazole hydrochloride, that acetoxyacetyl chloride was used instead of acetyl chloride, and that azetidine hydrochloride was used instead of dimethylamine hydrochloride.

Workup

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

Sources & evidence

ORD record
ord-82571852eb3948f28964317bbab5dc53
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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