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

HRID 1411302Notes

Reaction equation

HRID 1411302 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]([O:29]CC[Si](C)(C)C)=O)[C:10]2=[CH:11][CH:12]=1)C.[NH2:37][C:38]1[S:39][C:40]([CH3:43])=[CH:41][N:42]=1.C(OC[C:49](Cl)=[O:50])(=O)C.Cl.[NH:53]1[CH2:56][CH2:55][CH2:54]1>>[N:53]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])[CH2:49][OH:50])[CH2:16]4)[CH2:14][N:13]([C:27]([NH:37][C:38]4[S:39][C:40]([CH3:43])=[CH:41][N:42]=4)=[O:29])[C:10]3=[CH:11][CH:12]=2)[CH2:56][CH2:55][CH2:54]1

Participants

5

Reactant 4

HCID 26297Acetoxyacetyl chlorideHCID 3517702-Amino-5-methylthiazoleHCID 12308726Azetidine hydrochlorideHCID 904497641-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(3-ethoxy-3-oxopropyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

Product 1

HCID 904495295-(3-(azetidin-1-yl)-3-oxopropyl)-1'-(2-hydroxyacetyl)-N-(5-methylthiazol-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 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(3-ethoxy-3-oxopropyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate 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-methylthiazole 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-711b1c63ef4343b286c209bd48c29bb3
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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