Ammonia → N-[(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethyl]-[1,3,5]triazine-2,4,6-triamine

HRID 243408Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]3[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:13]=3[N:12]=2)[CH3:10])[N:5]=[C:4]([NH2:27])[N:3]=1.[NH3:28]>O1CCOCC1>[F:26][C:23]1[CH:24]=[CH:25][C:13]2[N:12]=[C:11]([C@@H:9]([NH:8][C:6]3[N:5]=[C:4]([NH2:27])[N:3]=[C:2]([NH2:28])[N:7]=3)[CH3:10])[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]=2[CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-chloro-N—[(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[1,3,5]triazine-2,4-diamine (100 mg, 0.26 mmol) in dioxane (1 mL) was added 880 NH3 (4 mL). The reaction mixture was heated at 100° C. for 1 h using microwave irradiation. After cooling to RT, the reaction mixture was evaporated and purified by column chromatography (Si—PCC, gradient 2-12% 2M NH3/MeOH in DCM) affording 286 as a pink foam (72.9 mg, 77%). LCMS (Method K): RT 2.89 min [M+H]+ 365.0. 1H NMR (DMSO-d6, 400 MHz, 80° C.): δ 7.67-7.60 (3H, m), 7.57-7.51 (3H, m), 7.05 (1H, ddd, J=10.1, 8.8, 2.6 Hz), 6.78 (1H, dd, J=9.0, 2.5 Hz), 6.31 (1H, bd, J=7.5 Hz), 5.61 (4H, bs), 5.22 (1H, quintet, J=7.1 Hz), 1.40 (3H, d, J=6.9 Hz)

Workup

custommicrowave irradiation
temperatureAfter cooling to RT
customthe reaction mixture was evaporated
custompurified by column chromatography (Si—PCC, gradient 2-12% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record: ord-876b00a7d09c4b2bb1a7d4f981701b03
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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