4-Hydroxypyrrolidine → 6-[2-(3-Hydroxy-pyrrolidin-1-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride

HRID 1853314Notes

Reaction equation

HRID 1853314 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][Cl:20])[CH:15]=2)[O:10][C:9]([C:21]2[N:26]=[CH:25][N:24]3[CH:27]=[CH:28][CH:29]=[C:23]3[CH:22]=2)=[CH:8]1)(C)(C)C.[NH:30]1[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31]1>>[ClH:20].[OH:35][CH:32]1[CH2:33][CH2:34][N:30]([CH2:19][CH2:18][O:17][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[O:10][C:9]([C:21]2[N:26]=[CH:25][N:24]4[CH:27]=[CH:28][CH:29]=[C:23]4[CH:22]=2)=[CH:8][C:7]3=[N:6][OH:5])[CH2:31]1

Participants

3

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 866730766-(2-chloro-ethoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime

Product 1

HCID 1317324746-[2-(3-Hydroxy-pyrrolidin-1-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride

Procedure

6-[2-(3-hydroxy-pyrrolidin-1-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride was prepared in 23% overall yield using the method described in example 87, starting from 6-(2-chloro-ethoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime (example 87B) and 3-pyrrolidinol.

Workup

  1. customoverall yield

Sources & evidence

ORD record
ord-26e92d4d32a241a3a2488b2fe324a426
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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