Tetrahydrofuran → HCID 117666830, compound

HRID 1526251Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@H:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[O:17][C:18]1[N:19]=[C:20]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([N:36]3[CH2:41][CH2:40][CH:39]([N:42]4[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]4)[CH2:38][CH2:37]3)=[CH:32][CH:31]=2)[C:21]([C:26]([NH2:28])=[O:27])=[N:22][C:23]=1[CH2:24][CH3:25].O.NN.O1CCCC1>C(O)C>[NH2:3][C@H:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[O:17][C:18]1[N:19]=[C:20]([NH:29][C:30]2[CH:31]=[CH:32][C:33]([N:36]3[CH2:37][CH2:38][CH:39]([N:42]4[CH2:43][CH2:44][N:45]([CH3:48])[CH2:46][CH2:47]4)[CH2:40][CH2:41]3)=[CH:34][CH:35]=2)[C:21]([C:26]([NH2:28])=[O:27])=[N:22][C:23]=1[CH2:24][CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-{[(1R,2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)cyclopentyl]oxy}-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (322 mg), hydrazine monohydrate (99 mg), tetrahydrofuran (6.44 mL), and ethanol (6.44 mL) was stirred at 80° C. overnight. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=99:1-97:3) to obtain 5-{[(1R,2S)-2-aminocyclopentyl]oxy}-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (117 mg) as a pale yellow solid.

Workup

customThe insoluble matter was separated by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=99:1-97:3)

Sources & evidence

ORD record: ord-6a4934bab8f148c88f215d0f119767d4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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