4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid → N-[(1R*,2R*,4R*)-4-Azido-2-fluorocyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide

HRID 1423513Notes

Reaction equation

HRID 1423513 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH:12]([F:14])[F:13])=[CH:8][C:7]=2[C:15]2[C:16]3[NH:23][C:22]([CH3:24])=[C:21]([C:25](O)=[O:26])[C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:3][CH2:2]1.Cl.[N:29]([C@H:32]1[CH2:37][CH2:36][C@H:35]([NH2:38])[C@@H:34]([F:39])[CH2:33]1)=[N+:30]=[N-:31]>>[N:29]([C@@H:32]1[CH2:37][CH2:36][C@@H:35]([NH:38][C:25]([C:21]2[C:17]3[N:18]=[CH:19][N:20]=[C:15]([C:7]4[CH:8]=[C:9]([CH:12]([F:14])[F:13])[CH:10]=[CH:11][C:6]=4[O:5][CH2:4][CH:1]4[CH2:2][CH2:3]4)[C:16]=3[NH:23][C:22]=2[CH3:24])=[O:26])[C@H:34]([F:39])[CH2:33]1)=[N+:30]=[N-:31]

Participants

3

Reactant 2

HCID 679560124-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acidHCID 86666656(1S*,2S*,4S*)-4-azido-2-fluorocyclohexanamine hydrochloride

Product 1

HCID 86666655N-[(1R*,2R*,4R*)-4-Azido-2-fluorocyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide

Procedure

Starting from 4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example D.g1) and (1S*,2S*,4S*)-4-azido-2-fluorocyclohexanamine hydrochloride (example C23) the title compound is obtained as pale yellow foam.

Sources & evidence

ORD record
ord-3a1950ae7da64df0a7af6db0e28607b4
Source dataset
uspto-grants-2015_01
Patent number
US08927557B2

Reaction notes

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