Diisopropylethylamine → HCID 68157691, compound

HRID 243484Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[C:9]([F:12])[CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C@@H:19]([NH2:21])[CH3:20])[CH3:2].[NH2:22][C:23]1[C:28]([C:29]#[N:30])=[C:27](Cl)[N:26]=[CH:25][N:24]=1.CCN(C(C)C)C(C)C>CC(O)C>[NH2:22][C:23]1[C:28]([C:29]#[N:30])=[C:27]([NH:21][C@H:19]([C:4]2[N:3]([CH2:1][CH3:2])[C:7]3[C:8]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=4)=[C:9]([F:12])[CH:10]=[CH:11][C:6]=3[N:5]=2)[CH3:20])[N:26]=[CH:25][N:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (S)-1-(1-ethyl-6-fluoro-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine (0.203 g, 0.715 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (0.11 g, 0.715 mmol) and DIPEA (0.65 mL, 3.58 mmol) in IPA (5 mL) was stirred at 80° C. in a sealed microwave tube for 16 hours. After cooling, the mixture was concentrated in vacuo and the residue was purified chromatography, (Si—PPC, gradient 0-5% MeOH in DCM), to give 410 as a solid (0.095 g, 33%). LCMS (Method K): RT 3.03 min [M+H]+ 403. 1H NMR (DMSO-d6, 400 MHz): δ 8.71-8.67 (1H, m), 7.96 (1H, s), 7.92 (1H, td, J=7.8, 1.9 Hz), 7.73 (1H, d, J=7.7 Hz), 7.70-7.62 (2H, m), 7.47 (1H, ddd, J=7.7, 5.0, 1.1 Hz), 7.25 (2H, br s), 7.12 (1H, dd, J=10.4, 8.8 Hz), 5.60 (1H, quin, J=7.2 Hz), 3.80-3.67 (2H, m), 1.55 (3H, d, J=6.8 Hz), 0.69 (3H, t, J=7.1 Hz)

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated in vacuo
customthe residue was purified chromatography, (Si—PPC, gradient 0-5% MeOH in DCM),

Sources & evidence

ORD record: ord-30dc5c3514ec4fffb60d655bdacd6e48
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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