N-methyl-2-pyrrolidone → HCID 66710560, compound

HRID 1261977Notes

Reaction equation

CS([C:4]1[N:16]=[CH:15][C:7]2=[CH:8][C:9]3[C:14]([N:6]2[N:5]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)=O.[CH2:17]1[N:22]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[CH2:21][CH2:20][O:19][CH2:18]1.CN1CCCC1=O>CO.ClCCl>[N:22]1([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:4]3[N:16]=[CH:15][C:7]4=[CH:8][C:9]5[C:14]([N:6]4[N:5]=3)=[CH:13][CH:12]=[CH:11][CH:10]=5)=[CH:27][CH:28]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 145 °C

Procedure

Into a 30 ml, vial 2-methanesulfinyl-[1,2,4]triazino[1,6-a]indole (50.00 mg, 0.216 mol), 4-(4-morpholino)aniline (84.8 mg, 0.476 mol), and N-methylpyrrolidinone (0.10 mL) were combined and heated at 145° C. for 2 hours. The reaction was cooled to room temperature and the product was isolated by flash chromatography (ISCO, Silicagel, methanol/dichloromethane 0-10%) to provide (4-morpholin-4-yl-phenyl)-[1,2,4]triazino[1,6-a]indol-2-yl-amine as a brown solid (14 mg, 19%). MP: 205-210° C.; 1H-NMR (CDCl3) δ 9.00 (s, 1H), 8.10 (d, J=8.5 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.68 (d, J=8.8 Hz, 2H), 7.42 (m, 1H), 7.31 (m, 1H), 6.99 (d, J=8.8 Hz, 2H), 6.94 (s, 1H), 6.80 (s, 1H), 3.89 (m, 4H), 3.16 (m, 4H); LC/MS (ESI+): 346.7 (M+H).

Workup

temperatureThe reaction was cooled to room temperature

Sources & evidence

ORD record: ord-30b73a7e2fd84ba5b3615527139028c6
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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