4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-3-carbaldehyde → 1-cyclopentyl-6-[(3S,4S)-4-methyl-1-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-ylmethyl)pyrrolidin-3-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424776Notes

Reaction equation

HRID 2424776 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[N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][C:25]2=[C:24]([CH:31]=O)[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]([CH2:31][C:24]5[CH:23]=[N:22][N:26]6[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=56)[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 450836804,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-3-carbaldehydeHCID 1361284551-cyclopentyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 1

HCID 1358759031-cyclopentyl-6-[(3S,4S)-4-methyl-1-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-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-cyclopentyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one and 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 7.99 (s, 1H), 7.35 (s, 1H), 5.16-5.09 (m, 1H), 4.11-4.06 (m, 2H), 3.68 (d, J=13.3 Hz, 1H), 3.57 (d, J=13.3 Hz, 1H), 3.32 (t, J=8.7 Hz, 1H), 3.00 (d, J=9.9 Hz, 1H), 2.94-2.80 (m, 2H), 2.78-2.77 (m, 1H), 2.49-2.45 (m, 1H), 2.38-2.33 (m, 1H), 2.11-1.83 (m, 11H), 1.73-1.61 (m, 2H), 1.17 (d, J=7.1 Hz, 3H). MS: (M+H m/z=422.1).

Sources & evidence

ORD record
ord-537b0e2862004c99a95a777e53cf12f2
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

Loading…