Diisopropylethylamine → HCID 57402937, compound

HRID 1261931Notes

Reaction equation

CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.C(N(CC)C(C)C)(C)C.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:38]=[C:39]([CH:41]=[CH:42][CH:43]=2)[NH2:40])[CH2:33][CH2:32]1>COCCO>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([NH:40][C:39]3[CH:41]=[CH:42][CH:43]=[C:37]([N:34]4[CH2:33][CH2:32][N:31]([CH3:30])[CH2:36][CH2:35]4)[CH:38]=3)=[N:5]2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 180 °C

Procedure

2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (75.0 mg, 0.000261 mol), N,N-Diisopropylethylamine (0.0682 mL, 0.000392 mol) and 3-(4-Methylpiperazin-1-yl)aniline (99.8 mg, 0.000522 mol) were dissolved in 2-Methoxyethanol (1.83 mL) and the reaction was heated under 300 W microwave conditions at 180° C. until HPLC showed consumption of starting material. The reaction mixture was then reduced en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 8.59 mg of [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine as lyophilated powder. (M+H)=415.18. 1H NMR (400 MHz, CDCl3) δ 10.42 (s, 1H), 8.55 (s, 1H), 7.87 (d, 1H, J=6.57 Hz), 7.52 (s, 1H), 7.30 (m, 3H), 7.18 (m, 2H), 7.09 (m, 2H), 6.57 (s, 1H), 3.84 (s, 3H), 3.55 (d, 2H, J=11.12 Hz), 3.45 (d, 2H, J=13.64 Hz), 3.18 (m, 2H), 2.90 (m, 2H), 2.86 (s, 3H).

Workup

customconsumption of starting material
customthe product was isolated
custompurified by Gilson prep HPLC

Sources & evidence

ORD record: ord-d86e4636502a464584ef2ac4d1b49af2
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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