2-Methoxyphenethylamine → HCID 66991174, compound

HRID 2367249Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([NH2:17])=[N:13][NH:14]3)=[CH:10][CH:9]=2)[CH:5]=[C:4](S(C)(=O)=O)[N:3]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][NH2:32].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[NH2:17][C:12]1[C:11]2[C:15](=[CH:16][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:32][CH2:31][CH2:30][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[O:23][CH3:22])[CH:5]=3)=[CH:9][CH:10]=2)[NH:14][N:13]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 6-[2-amino-6-(methylsulfonyl)-4-pyrimidinyl]-1H-indazol-3-amine (500 mg, 1.64 mmol), 2-[2-(methyloxy)phenyl]ethanamine (500 mg, 3.31 mmol), and Hunig's base (2 mL) in NMP (3 mL) was heated for 4 hours at 140° C. in a BiotageInitiator® microwave synthesizer. Upon cooling, the mixture was decanted to remove the solids, and the resulting solution was concentrated to dryness. The crude material was purified by RPHPLC (gradient: 10% CH3CN/H2O to 30% CH3CN/H2O) to afford the title compound (100 mg) as a yellow solid. LC-MS (ES) m/z=376 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 2.81-2.84 (m, 2H), 3.52 (m, 2H), 3.74 (s, 3H), 5.37 (s, 2H), 6.01 (s, 2H), 6.28 (s, 1H), 6.76-6.86 (m, 4H), 7.22 (t, J=8.4 Hz, 1H), 7.41 (d, J=7.6 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.84 (s, 1H), 11.51 (s, 1H).

Workup

temperatureUpon cooling
customthe mixture was decanted
customto remove the solids
concentrationthe resulting solution was concentrated to dryness
customThe crude material was purified by RPHPLC (gradient: 10% CH3CN/H2O to 30% CH3CN/H2O)

Sources & evidence

ORD record: ord-a9bab1ddec01444980db7e442345b9be
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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