(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrobromide → 6-[(1S,4S)-2-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride

HRID 1853325Notes

Reaction equation

HRID 1853325 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.[C@H:30]12[CH2:36][C@H:33]([NH:34][CH2:35]1)[CH2:32][O:31]2>>[ClH:20].[C@H:30]12[CH2:36][C@H:33]([N:34]([CH2:19][CH2:18][O:17][C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[O:10][C:9]([C:21]3[N:26]=[CH:25][N:24]5[CH:27]=[CH:28][CH:29]=[C:23]5[CH:22]=3)=[CH:8][C:7]4=[N:6][OH:5])[CH2:35]1)[CH2:32][O:31]2

Participants

3

Reactant 2

HCID 11159293(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrobromideHCID 866730766-(2-chloro-ethoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime

Product 1

HCID 1317324826-[(1S,4S)-2-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride

Procedure

6-[(1S,4S)-2-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)-ethoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime, hydrochloride was prepared in 37% 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 (1S,4S)-2-oxa-5-aza-bicyclo[2.2.1]heptane.

Workup

  1. customoverall yield

Sources & evidence

ORD record
ord-8dcd2647d25b4bf4bd8a2095cae25e0f
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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