1-Methyl-1H-imidazo(4,5-c)pyridine-2-carboxaldehyde → 6-{(3S,4S)-4-methyl-1-[(1-methyl-1H-imidazo[4,5-c]pyridin-2-yl)methyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424799Notes

Reaction equation

HRID 2424799 reaction equation
[CH3:1][C@@H:2]1[CH2:6][N:5](CC2C=NC(C)=NC=2)[CH2:4][C@H:3]1[C:15]1[NH:16][C:17](=[O:30])[C:18]2[CH:23]=[N:22][N:21]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:19]=2[N:20]=1.[CH3:31][N:32]1[C:40]2[CH:39]=[CH:38][N:37]=[CH:36][C:35]=2[N:34]=[C:33]1[CH:41]=O>>[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:41][C:33]2[N:32]([CH3:31])[C:40]3[CH:39]=[CH:38][N:37]=[CH:36][C:35]=3[N:34]=2)[CH2:4][C@H:3]1[C:15]1[NH:16][C:17](=[O:30])[C:18]2[CH:23]=[N:22][N:21]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:19]=2[N:20]=1

Participants

3

Reactant 2

HCID 122393311-Methyl-1H-imidazo(4,5-c)pyridine-2-carboxaldehydeHCID 1358864606-((3S,4S)-4-Methyl-1-((2-methylpyrimidin-5-YL)methyl)pyrrolidin-3-YL)-1-(tetrahydro-2H-pyran-4-YL)-1,5-dihydro-4H-pyrazolo[3,4-D]pyrimidin-4-one

Product 1

HCID 1358864716-{(3S,4S)-4-methyl-1-[(1-methyl-1H-imidazo[4,5-c]pyridin-2-yl)methyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Procedure

Following the procedure for the preparation of 6-{(3S,4S)-4-methyl-1-[(2-methylpyrimidin-5-yl)methyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting 1-methyl-1H-imidazo[4,5-c]pyridine-2-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 10.83 (brs 1H), 9.01 (s, 1H), 8.41 (d, J=15.8 Hz, 1H), 7.98 (s, 1H), 7.30 (d, J=4.98 Hz, 1H), 4.79-4.75 (m, 1H), 4.13-4.06 (m, 3H), 4.00-3.96 (s, 4H), 3.60-3.52 (m, 2H), 3.30 (t, J=8.7 Hz, 1H), 3.07 (d, J=9.9 Hz, 1H), 2.92-2.89 (m, 1H), 2.82-2.77 (m, 1H), 2.48-2.45 (m, 1H), 2.36-2.27 (m, 2H), 2.19-2.17 (m, 1H), 1.89-1.79 (m, 2H), 1.23 (d, J=6.6 Hz, 3H). MS: (M+H m/z 449.2).

Sources & evidence

ORD record
ord-1941f67f11b941eca1044a7d23236715
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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