Piperidine → HCID 178428328, compound

HRID 2046973Notes

Reaction equation

HRID 2046973 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[C:15]([O:17][CH:18]([CH3:20])[CH3:19])[C:14]([NH:21][C:22]3[N:27]=[C:26]4[NH:28][N:29]=[C:30]([CH3:31])[C:25]4=[C:24]([NH:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[S:39]([CH:42]([CH3:44])[CH3:43])(=[O:41])=[O:40])[N:23]=3)=[CH:13][C:12]=2[CH3:45])[CH2:7][CH2:6]1)=[O:4].[NH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C=O)C>[CH:18]([O:17][C:15]1[C:14]([NH:21][C:22]2[N:27]=[C:26]3[NH:28][N:29]=[C:30]([CH3:31])[C:25]3=[C:24]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[S:39]([CH:42]([CH3:43])[CH3:44])(=[O:41])=[O:40])[N:23]=2)=[CH:13][C:12]([CH3:45])=[C:11]([CH:8]2[CH2:7][CH2:6][N:5]([C:3](=[O:4])[CH2:2][N:46]3[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]3)[CH2:10][CH2:9]2)[CH:16]=1)([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 178428327HCID 178428327, compound

Product 1

HCID 178428328HCID 178428328, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-1-(4-(5-isopropoxy-4-(4-(2-(isopropylsulfonyl)phenylamino)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylphenyl)piperidin-1-yl)ethanone from Example 8 (10 mg, 0.014 mmol), and piperidine (3 uL, 0.031 mmol) in DMF was stirred at rt overnight. The crude mixture was directly purified by reverse phase HPLC to give 1-(4-(5-isopropoxy-4-(4-(2-(isopropylsulfonyl)phenylamino)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylphenyl)piperidin-1-yl)-2-(piperidin-1-yl)ethanone. MS: m/z=703.4 (M+1), 352.2 (M/2+1). 1H-NMR (400 MHz, CD3OD): δ=8.39 (brs, 1H), 7.98 (dd, 1H, J=1.6, 8.0 Hz), 7.70 (t, 1H, J=7.6 Hz), 7.53-7.49 (m, 2H), 6.88 (s, 1H), 4.73-4.69 (m, 1H), 4.62 (sept, 1H, J=6.0 Hz), 4.31 (d, 1H, J=16.4 Hz), 4.22 (d, 1H, J=16.4 Hz), 3.85-3.82 (m, 1H), 3.60 (t, 2H, J=12.0 Hz), 3.41-3.25 (m, 2H), 3.11-3.00 (m, 3H), 2.90-2.84 (m, 1H), 2.79 (s, 3H), 2.22 (s, 3H), 1.99-1.85 (m, 7H), 1.80-1.54 (m, 3H), 1.27 (d, 6H, J=6.0 Hz), 1.24 (d, 6H, J=6.8 Hz).

Workup

  1. customThe crude mixture was directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d25e4c1e98604e918173fd48817cd175
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

Loading…