2,1,3-Benzothiadiazole-5-carbaldehyde → 6-[(3S,4S)-1-(2,1,3-benzothiadiazol-5-ylmethyl)-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424800Notes

Reaction equation

HRID 2424800 reaction equation
[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:9]=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.[N:31]1[S:32][N:33]=[C:34]2[CH:39]=C(C=O)C=[CH:36][C:35]=12>>[N:31]1[S:32][N:33]=[C:34]2[CH:39]=[C:8]([CH2:7][N:5]3[CH2:6][C@@H:2]([CH3:1])[C@H:3]([C:15]4[NH:16][C:17](=[O:30])[C:18]5[CH:23]=[N:22][N:21]([CH:24]6[CH2:29][CH2:28][O:27][CH2:26][CH2:25]6)[C:19]=5[N:20]=4)[CH2:4]3)[CH:9]=[CH:36][C:35]=12

Participants

3

Reactant 2

HCID 27762902,1,3-Benzothiadiazole-5-carbaldehydeHCID 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 1358864806-[(3S,4S)-1-(2,1,3-benzothiadiazol-5-ylmethyl)-4-methylpyrrolidin-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 benzo[c][1,2,5]thiadiazole-5-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 10.97 (brs, 1H), 8.02-8.00 (m, 2H), 7.86 (s, 1H), 7.77 (d, J=1.2 Hz, 1H), 4.81-4.75 (m, 1H), 4.12-4.06 (m, 2H), 3.96-3.92 (m, 1H), 3.81-3.78 (m, 1H), 3.60-3.52 (m, 2H), 3.38 (t, J=8.3 Hz, 1H), 3.03 (d, J=9.9 Hz, 1H), 2.88-2.85 (m, 1H), 2.68-2.63 (m, 1H), 2.47-2.45 (m, 1H), 2.37-2.28 (m, 2H), 2.04 (t, J=8.7 Hz, 1H), 1.90-1.80 (m, 2H), 1.21 (d, J=7.1 Hz, 3H). MS: (M+H m/z 452.1).

Sources & evidence

ORD record
ord-605b331da37447ce950be8eaab258dd3
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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