Methylamine → HCID 57756229, compound

HRID 911162Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[N:24][N:23]=3)=[CH:17][CH:16]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:44][NH2:45]>C1COCC1>[CH3:44][NH:45][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[N:24][N:23]=3)=[CH:17][CH:16]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A high pressure steel bomb was charged with N-(4-(3-(2-fluoropyridin-4-yl)pyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine (0.115 g, 0.237 mmol), potassium carbonate (0.049 g, 0.355 mol) and 3.0 mL of THF. The bomb was sealed, cooled to 0° C. and pressurized with methylamine gas. The reaction mixture was allowed to warm to RT, and heated at 80° C. for 45 h. Upon cooling, the reaction mixture was filtered through a fritted funnel, washed with MeOH, and concentrated. This mixture was purified by silica gel chromatography, (ISCO, 40 g column 0-10% MeOH/dichloromethane) to provide N-(4-(3-(2-(methylamino)pyridin-4-yl)pyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine as a light yellow solid. MS m/z=497 [M+H]+. Calc'd for C31H24N6O: 496.56.

Workup

customThe bomb was sealed
temperatureto warm to RT
temperatureheated at 80° C. for 45 h
temperatureUpon cooling
filtrationthe reaction mixture was filtered through a fritted funnel
washwashed with MeOH
concentrationconcentrated
customThis mixture was purified by silica gel chromatography, (ISCO, 40 g column 0-10% MeOH/dichloromethane)

Sources & evidence

ORD record: ord-880d439bccdc41b7b22f03d7cb564dc3
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022221B2

Reaction notes

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