Ammonia → HCID 68228381, compound

HRID 1521877Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([N:10]2[C:14]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[S:21](=[O:24])(=[O:23])[CH2:22][C:13]=3[C:12]([C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[O:26])=[N:11]2)[CH2:5]1.[NH3:33]>CC#N>[N:27]1([C:25]([C:12]2[C:13]3[CH2:22][S:21](=[O:24])(=[O:23])[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:14]=3[N:10]([CH:6]3[CH2:7][CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH2:33])[CH2:5]3)[N:11]=2)=[O:26])[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of enantiomer B of 1-[1-(2-chloroethyl)piperidin-3-yl]-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (90 mg; 0.19 mmol; 1.00 eq.) in CH3CN (0.90 ml) is added aq ammonia (181.88 μl; 2.82 mmol; 15.00 eq.) and the reaction is stirred at 135° C. for 15 min under microwave irradiation which after purification by MD-Autoprep affords the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz): δ 8.05 (d, J=7.8 Hz, 1H), 7.96 (t, J=7.1 Hz, 1H), 7.87 (d, J=7.6 Hz, 1H), 7.75 (t, J=7.4 Hz, 1H), 4.79 (q, J=16.2 Hz, 3H), 3.90 (s, 2H), 3.66 (s, 6H), 3.15 (d, J=9.7 Hz, 2H), 2.90 (q, J=13.0 Hz, 3H), 2.73-2.53 (m, 2H), 2.27-2.02 (m, 2H), 2.00-1.59 (m, 3H). MS (ESI+): 460.3. HPLC (max plot) 55.4%; Rt 2.09 min.

Workup

customafter purification

Sources & evidence

ORD record: ord-c658d9ee33f04386929a3eac4be6444f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073940B2

Reaction notes

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