1-Benzyl-4-methyl-pyrrolidine-3-carboxylic acid methyl ester → 6-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-thiopyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424818Notes

Reaction equation

HRID 2424818 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][S:10][CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[C:13]([NH2:15])=[O:14].CO[C:18]([C@H:20]1[C@H:24]([CH3:25])[CH2:23][N:22]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:21]1)=O>>[CH2:26]([N:22]1[CH2:23][C@@H:24]([CH3:25])[C@H:20]([C:18]2[NH:15][C:13](=[O:14])[C:3]3[CH:4]=[N:5][N:6]([CH:7]4[CH2:12][CH2:11][S:10][CH2:9][CH2:8]4)[C:2]=3[N:1]=2)[CH2:21]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 65589731-Benzyl-4-methyl-pyrrolidine-3-carboxylic acid methyl esterHCID 575562125-amino-1-(tetrahydro-2H-thiopyran-4-yl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1358864986-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-thiopyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Procedure

Following the procedure for the preparation of 6-[(3,4-trans)-1-benzyl-4-methylpyrrolidin-3-yl]-1-(2-methoxyphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting 5-amino-1-(tetrahydro-2H-thiopyran-4-yl)-1H-pyrazole-4-carboxamide and (3S,4S)-methyl-1-benzyl-4-methylpyrrolidine-3-carboxylate provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.02 (s, 1H), 7.41-7.26 (m, 5H), 4.60-4.53 (m, 1H), 3.86-3.83 (m, 1H), 3.65 (m, 1H), 3.41-3.37 (m, 1H), 3.02 (m, 1H), 2.94-2.75 (m, 4H), 2.60-2.31 (m, 3H), 2.25-2.16 (m, 2H), 1.99-1.94 (m, 1H), 1.62 (m, 2H), 1.20 (t, J=7.1 Hz, 3H). MS: (M+H m/z 410.2).

Sources & evidence

ORD record
ord-4663bc4823ae450da9234558d184d0a0
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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