Methylamine → N-(2,6-Diethylphenyl)-1-methyl-8-[(1-{[3-(methylamino)propyl]sulfonyl}piperidin-4-yl)amino]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide hydrochloride

HRID 81956Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:24]=[CH:23][C:22]3[CH2:21][CH2:20][C:19]4[C:25]([C:29]([NH:31][C:32]5[C:37]([CH2:38][CH3:39])=[CH:36][CH:35]=[CH:34][C:33]=5[CH2:40][CH3:41])=[O:30])=[N:26][N:27]([CH3:28])[C:18]=4[C:17]=3[N:16]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].[CH3:42][NH2:43]>O1CCCC1.ClCCl.CO>[ClH:1].[CH2:38]([C:37]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:40][CH3:41])[C:32]=1[NH:31][C:29]([C:25]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:23]=[N:24][C:15]([NH:14][CH:11]4[CH2:12][CH2:13][N:8]([S:5]([CH2:4][CH2:3][CH2:2][NH:43][CH3:42])(=[O:7])=[O:6])[CH2:9][CH2:10]4)=[N:16][C:17]=3[C:18]=2[N:27]([CH3:28])[N:26]=1)=[O:30])[CH3:39]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 8-({1-[(3-chloropropyl)sulfonyl]piperidin-4-yl}amino)-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (30 mg, 0.050 mmol) in tetrahydrofurane (2 mL) in a sealed tube, methylamine (40% aqueous solution) (0.5 mL) was added. The mixture was then heated at 60° C. for 20 h. Solvent evaporated to dryness and the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol: 8/2) to 23 mg of the title compound (76% yield).

Workup

customSolvent evaporated to dryness

Sources & evidence

ORD record: ord-362b87dfaf9d4983a79d9f9e7399a29e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846701B2

Reaction notes

Loading…