Quinoxaline-6-carboxaldehyde → PF-4181366

HRID 2424768Notes

Reaction equation

HRID 2424768 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([C@H:16]4[C@H:20]([CH3:21])[CH2:19][NH:18][CH2:17]4)[NH:13][C:14](=[O:15])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:22]1[C:31]2[C:26](=[CH:27][C:28]([CH:32]=O)=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1>>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([C@H:16]4[C@H:20]([CH3:21])[CH2:19][N:18]([CH2:32][C:28]5[CH:27]=[C:26]6[C:31](=[CH:30][CH:29]=5)[N:22]=[CH:23][CH:24]=[N:25]6)[CH2:17]4)[NH:13][C:14](=[O:15])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 763958Quinoxaline-6-carboxaldehydeHCID 1361284551-cyclopentyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 135564899PF-4181366

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-cyclopentyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one and quinoxaline-6-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.82 (s, 2H), 8.14 (d, J=8.3 Hz, 1H), 8.07-7.93 (m, 3H), 5.15-5.08 (m, 1H), 4.00-3.87 (m, 2H), 3.37 (t, J=8.7 Hz, 1H), 3.04 (d, J=9.5 Hz, 1H), 2.85-2.84 (m, 1H), 2.66-2.62 (m, 1H), 2.46-2.42 (m, 1H), 2.11-1.92 (m, 7H), 1.71-1.63 (m, 2H), 1.20 (d, J=7.05 Hz, 3H), MS: (M+H m/z=430.1).

Sources & evidence

ORD record
ord-6d8b45bfd67d4dffa677059083402cf7
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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