Diisopropylethylamine → HCID 66991412, compound

HRID 2367248Notes

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.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][NH2:31].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:31][CH2:30][CH2:29][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[F: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-fluorophenyl)ethanamine (500 mg, 2.19 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: 20% CH3CN/H2O to 40% CH3CN/H2O) to afford the title compound (166 mg) as a yellow solid. LC-MS (ES) m/z=364 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 2.86-2.90 (m, 2H), 3.49-3.51 (m, 2H), 5.35 (s, 2H), 5.98 (s, 2H), 6.25 (s, 1H), 6.97 (s, 1H), 7.12-7.17 (m, 2H), 7.23-7.29 (m, 1H), 7.33-7.41 (m, 2H), 7.68 (d, J=8.4 Hz, 1H), 7.82 (s, 1H), 11.50 (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: 20% CH3CN/H2O to 40% CH3CN/H2O)

Sources & evidence

ORD record: ord-f1eef066b1514934b0d70c528f5fdf30
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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