Pyrido[2,3-b]pyrazine-8-carbaldehyde → 1-isopropyl-6-[(3S,4S)-4-methyl-1-(pyrido[2,3-b]pyrazin-8-ylmethyl)pyrrolidin-3-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424790Notes

Reaction equation

HRID 2424790 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[CH:25]=[CH:24][N:23]=[C:22]2[N:26]=[CH:27][CH:28]=[C:29]([CH:30]=O)[C:21]=12>>[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:29]4[C:21]5[C:22](=[N:23][CH:24]=[CH:25][N:20]=5)[N:26]=[CH:27][CH:28]=4)[CH2:15]3)[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 42281362Pyrido[2,3-b]pyrazine-8-carbaldehydeHCID 1361284601-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 1358759211-isopropyl-6-[(3S,4S)-4-methyl-1-(pyrido[2,3-b]pyrazin-8-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 pyrido[2,3-b]pyrazine-8-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 10.00 (brs, 1H), 9.16-9.10 (m, 3H), 8.00 (s, 1H), 7.78 (m, 1H), 5.00-4.97 (m, 1H), 4.63-4.58 (m, 1H), 4.34-4.18 (m, 1H), 3.30 (m, 1H), 3.27 (m, 1H), 2.92-2.77 (m, 2H), 2.49-2.38 (m, 1H), 2.09-1.97 (m, 1H), 1.48 (dd, J=10.8, 6.6 Hz, 6H), 1.20 (d, J=6.6 Hz, 3H). MS: (M+H m/z 405.2).

Sources & evidence

ORD record
ord-6e6dec779f3d4e66b28f379e3df4aee2
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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