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

HRID 2424772Notes

Reaction equation

[CH:1]([N:4]1[C:8]2[N:9]=[C:10]([C@H:14]3[C@H:18]([CH3:19])[CH2:17][NH:16][CH2:15]3)[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2].[N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]([CH:30]=O)[CH:21]=1>>[CH:1]([N:4]1[C:8]2[N:9]=[C:10]([C@H:14]3[C@H:18]([CH3:19])[CH2:17][N:16]([CH2:30][C:22]4[CH:21]=[N:20][C:29]5[C:24]([CH:23]=4)=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:15]3)[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 836413-Quinolinecarboxaldehyde

HCID 1361284601-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 1358759111-isopropyl-6-[(3S,4S)-4-methyl-1-(quinolin-3-ylmethyl)pyrrolidin-3-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Procedure

Following the procedure for the preparation of 1-cyclopentyl-6-[(3,4-trans)-4-methyl-1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting 1-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one and quinoline-3-carbaldehyde provided the title compound. 400 MHz 1H NMR (CD3OD) δ 11.0 (brs, 1H), 8.87 (d, J=2.1 Hz, 1H), 8.29 (s, 1H), 8.07 (d, J=8.3 Hz, 1H), 8.02 (s, 1H), 7.90-7.88 (m, 1H), 7.70-7.66 (m, 1H), 7.56-7.51 (m, 1H), 5.01-4.92 (m, 1H), 4.03-3.83 (m, 2H), 3.40 (t, J=8.7 Hz, 1H), 3.07 (d, J=9.5 Hz, 1H), 2.89-2.86 (m, 1H), 2.68-2.67 (m, 1H), 2.48-2.47 (m, 1H), 2.08-2.02 (m, 1H), 1.48 (dd, J=6.6, 16.59 Hz, 6H), 1.20 (J=7.1 Hz, 3H). MS: (M+H m/z 403.1).

Sources & evidence

ORD record: ord-7476a7790a4f461e906795483375d235
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

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