Methylamine → 1-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(2-hydroxy-acetylamino)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid (pyridin-2-ylmethyl)-amide

HRID 1882626Notes

Reaction equation

HRID 1882626 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[C@@H:19]3[CH2:23][C@H:22]([NH:24][C:25](=[O:28])[CH2:26]C)[C@@H:21]([OH:29])[C@H:20]3[OH:30])=[C:12]([NH:31][CH2:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:11]=2)[CH:9]=1)=[O:4].C([O:48]C(C1C=NN(C2N=C3C(N=CN3[C@@H]3C[C@H](NC(=O)CC)[C@@H](O)[C@H]3O)=C(NCC(C3C=CC=CC=3)C3C=CC=CC=3)N=2)C=1)=O)C.[N:92]1[CH:97]=[CH:96][CH:95]=[CH:94][C:93]=1CN.CN>>[N:92]1[CH:97]=[CH:96][CH:95]=[CH:94][C:93]=1[CH2:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[C@@H:19]3[CH2:23][C@H:22]([NH:24][C:25](=[O:28])[CH2:26][OH:48])[C@@H:21]([OH:29])[C@H:20]3[OH:30])=[C:12]([NH:31][CH2:32][CH:33]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:11]=2)[CH:9]=1)=[O:4]

Participants

5

Reactant 4

HCID 6329MethylamineHCID 195092-PyridinemethanamineHCID 666301851-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid methylamideHCID 666305741-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 666306431-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(2-hydroxy-acetylamino)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid (pyridin-2-ylmethyl)-amide

Procedure

The title compound is prepared analogously to 1-[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid methylamide (Example 173), by substituting 1-[9-[(1R,2S,3R,4S)-2,3-dihydroxy-4-(2-hydroxy-acetylamino)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (Intermediate ZS) for 1-[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (Example 173, step 1) and C-pyridin-2-yl-methylamine for methylamine.

Sources & evidence

ORD record
ord-2ee584fc944b4ddb814c7bd681446658
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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