tert-butyl N-[(3S)-piperidin-3-yl]carbamate → (S)-1-(3-methyl-6-(6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amine

HRID 57907Notes

Reaction equation

HRID 57907 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7]C(=O)OC(C)(C)C)[CH2:2]1.Br[C:16]1[N:21]=[C:20](F)[C:19]([CH3:23])=[CH:18][CH:17]=1.[CH3:24][C:25]1[N:30]=[C:29]([C:31]2[N:36]=[CH:35][C:34]3[CH:37]=[N:38][NH:39][C:33]=3[CH:32]=2)[CH:28]=[N:27][CH:26]=1>>[CH3:23][C:19]1[C:20]([N:1]2[CH2:6][CH2:5][CH2:4][C@H:3]([NH2:7])[CH2:2]2)=[N:21][C:16]([N:39]2[C:33]3[CH:32]=[C:31]([C:29]4[CH:28]=[N:27][CH:26]=[C:25]([CH3:24])[N:30]=4)[N:36]=[CH:35][C:34]=3[CH:37]=[N:38]2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 573366426-Bromo-2-fluoro-3-methylpyridineHCID 867070806-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 86707099(S)-1-(3-methyl-6-(6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amineYield 4.5%

Procedure

Following the procedures as described in EXAMPLE 86 and starting with tert-butyl N-[(3S)-3-piperidyl]carbamate, 6-bromo-2-fluoro-3-methyl-pyridine, and 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine, 205 was obtained as an off-white solid (4.4 mg, 4.5%) over 3 steps. 1H NMR (400 MHz, DMSO) δ 9.75-9.70 (s, 1H), 9.48-9.44 (s, 1H), 9.33-9.29 (s, 1H), 8.68-8.61 (d, J=12.1 Hz, 2H), 8.38-8.15 (s, 1H), 7.78-7.74 (d, J=8.1 Hz, 1H), 7.59-7.55 (d, J=8.0 Hz, 1H), 2.90-2.84 (m, 1H), 2.67-2.63 (s, 3H), 2.37-2.32 (s, 3H), 2.04-1.95 (d, J=9.2 Hz, 2H), 1.80-1.68 (d, J=9.4 Hz, 1H), 1.57-1.47 (d, J=8.6 Hz, 1H); MS (ESI) m/z: 433.1 [M+H]+

Sources & evidence

ORD record
ord-24d5e191c29046b89835d69a8a926f13
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

Loading…