1-(2-Chloroethyl)-3,3-difluoropyrrolidine Hydrochloride → 6-[2-(3,3-Difluoro-pyrrolidin-1-yl)-ethoxy]-2-thieno[3,2-c]pyridin-6-yl-chromen-4-one oxime, hydrochloride

HRID 1853347Notes

Reaction equation

HRID 1853347 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[O:10][C:9]([C:18]2[N:23]=[CH:22][C:21]3[CH:24]=[CH:25][S:26][C:20]=3[CH:19]=2)=[CH:8]1)(C)(C)C.Cl.[Cl:28][CH2:29][CH2:30][N:31]1[CH2:35][CH2:34][C:33]([F:37])([F:36])[CH2:32]1>>[ClH:28].[F:36][C:33]1([F:37])[CH2:34][CH2:35][N:31]([CH2:30][CH2:29][O:17][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[O:10][C:9]([C:18]2[N:23]=[CH:22][C:21]4[CH:24]=[CH:25][S:26][C:20]=4[CH:19]=2)=[CH:8][C:7]3=[N:6][OH:5])[CH2:32]1

Participants

3

Reactant 2

HCID 671974041-(2-Chloroethyl)-3,3-difluoropyrrolidine HydrochlorideHCID 866731016-Hydroxy-2-thieno[3,2-c]pyridin-6-yl-chromen-4-one O-tert-butyl-oxime

Product 1

HCID 1371875866-[2-(3,3-Difluoro-pyrrolidin-1-yl)-ethoxy]-2-thieno[3,2-c]pyridin-6-yl-chromen-4-one oxime, hydrochloride

Procedure

6-[2-(3,3-Difluoro-pyrrolidin-1-yl)-ethoxy]-2-thieno[3,2-c]pyridin-6-yl-chromen-4-one oxime, hydrochloride was prepared in 62% overall yield using the method described in example 127, starting from 6-Hydroxy-2-thieno[3,2-c]pyridin-6-yl-chromen-4-one O-tert-butyl-oxime (example 127B) and 1-(2-Chloro-ethyl)-3,3-difluoro-pyrrolidine hydrochloride (WO2008/86404).

Workup

  1. customoverall yield

Sources & evidence

ORD record
ord-9046dd4bbdd64a41bc6a7680c2a3fa4b
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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