4-Quinolinecarboxaldehyde → 6-[(3S,4S)-4-methyl-1-(quinolin-4-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424801Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7]C2C=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[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34](C=O)=[CH:33][CH:32]=1>>[CH3:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:34]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:31]=[CH:32][CH:33]=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[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:19]=2[N:20]=1

Participants

Reactant 2

HCID 780724-Quinolinecarboxaldehyde

HCID 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 1358864796-[(3S,4S)-4-methyl-1-(quinolin-4-ylmethyl)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 quinoline-4-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 10.68 (brs, 1H), 8.83 (d, J=4.1 Hz, 1H), 8.25-8.22 (m, 1H), 8.12-8.08 (m, 1H), 7.98 (s, 1H), 7.75-7.72 (m, 1H), 7.54 (d, J=3.3 Hz, 1H), 7.36 (d, J=3.3 Hz, 1H), 5.21 (m, 1H), 4.77 (m, 1H), 4.13-4.06 (m, 3H), 3.59-3.52 (m, 2H), 3.32 (d, J=8.7 Hz, 1H), 3.03 (d, J=9.9 Hz, 1H), 2.88-2.86 (m, 1H), 2.72-2.69 (m, 1H), 2.36-2.28 (m, 3H), 2.04-2.00 (m, 1H), 1.89-1.84 (m, 2H), 1.20 (d, J=7.1 Hz, 3H). MS: (M+H m/z 445.1).

Sources & evidence

ORD record: ord-d9344787fe234cecbb4c09112a88a2a7
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

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