L-Prolinol → 6-[2-((S)-2-hydroxymethylpyrrolidin-1-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride

HRID 1853312Notes

Reaction equation

HRID 1853312 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.[OH:30][CH2:31][C@@H:32]1[CH2:36][CH2:35][CH2:34][NH:33]1>>[ClH:20].[OH:30][CH2:31][C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[CH2:19][CH2:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([C:21]1[N:26]=[CH:25][N:24]3[CH:27]=[CH:28][CH:29]=[C:23]3[CH:22]=1)=[CH:8][C:7]2=[N:6][OH:5]

Participants

3

Reactant 2

HCID 640091L-ProlinolHCID 866730766-(2-chloro-ethoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime

Product 1

HCID 1317324726-[2-((S)-2-hydroxymethylpyrrolidin-1-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride

Procedure

6-[2-((S)-2-hydroxymethylpyrrolidin-1-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride was prepared in 8% 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 2-((S)-2-hydroxymethylpyrrolidine.

Workup

  1. customoverall yield

Sources & evidence

ORD record
ord-0d6837b51d8e464db3f84e14c86a9526
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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