HCID 178464640, compound → HCID 178464641, compound

HRID 1044700Notes

Reaction equation

[CH2:1]([NH:3][C:4]([N:18]1[CH2:22][CH:21]([CH2:23][CH3:24])[CH:20]=[N:19]1)=[N:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][NH:15]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2]>C1(C)C=CC=CC=1>[CH2:1]([NH:3][C:4]([N:18]1[CH2:22][CH:21]([CH2:23][CH3:24])[CH:20]=[N:19]1)=[N:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)(=[O:7])=[O:8])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

0.14 g 2,3-Dihydro-1H-indole-6-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide was dissolved in 25 mL toluene, the mixture was degassed, and 10 mol % of palladium on carbon was added. The mixture was stirred overnight at 50° C. The mixture was cooled to room temperature and filtered over Hyflo, and the Hyflo was washed with toluene. The filtrate was evaporated to dryness and the residue was purified by flash chromatography (DCM→DCM/EA 95:5→DCM/EA 8:2) to give 70 mg of 1H-Indole-6-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide as a white amorphous solid. 1H NMR (400 MHz, CDCl3) δ 0.86 (t, J=7.52 Hz, 3H), 1.06 (t, J=7.22 Hz, 3H), 1.32-1.57 (m, 2H), 2.89-3.00 (m, 1H), 3.35-3.54 (m, 3H), 3.89 (t, J=11.44 Hz, 1H), 6.54 (br.s., 1H), 6.84 (d, J=1.50 Hz, 1H), 6.96 (br.s., 1H), 7.36 (t, J=2.86 Hz, 1H), 7.59-7.70 (m, 2H), 8.26 (d, J=1.20 Hz, 1H), 9.55 (br.s., 1H).

Workup

customthe mixture was degassed
addition10 mol % of palladium on carbon was added
temperatureThe mixture was cooled to room temperature
filtrationfiltered over Hyflo
washthe Hyflo was washed with toluene
customThe filtrate was evaporated to dryness
customthe residue was purified by flash chromatography (DCM→DCM/EA 95:5→DCM/EA 8:2)

Sources & evidence

ORD record: ord-153d59b2c8fe46f49e74e7236e1b9709
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563723B2

Reaction notes

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