Diisopropylethylamine → HCID 68157857, compound

HRID 243485Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

(S)-1-(6-Fluoro-1-methyl-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine (0.093 g, 0.35 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (53 mg, 0.35 mmol) and DIPEA (313 μL, 1.72 mmol) in IPA (5 mL) were added and the reaction mixture heated at 90° C. for 16 h. The reaction mixture was concentrated in vacuo and the resultant residue purified by flash chromatography (Si—PPC, gradient 0-10% methanol in DCM) to give 411 as a white solid (95 mg, 72%). LCMS (Method K): RT 2.76 min [M+H]+ 389. 1H NMR (DMSO-d6, 400 MHz): δ 8.70 (1H, ddd, J=4.8, 1.7, 0.9 Hz), 7.98 (1H, s), 7.91 (1H, td, J=7.8, 1.8 Hz), 7.71-7.64 (2H, m), 7.60 (1H, dq, J=7.7, 0.9 Hz), 7.46 (1H, ddd, J=7.6, 4.9, 1.0 Hz), 7.26 (2H, br s), 7.11 (1H, dd, J=10.5, 8.8 Hz), 5.59 (1H, quin, J=7.3 HZ), 3.09 (3H, s), 1.53 (3H, d, J=6.8 Hz)

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe resultant residue purified by flash chromatography (Si—PPC, gradient 0-10% methanol in DCM)

Sources & evidence

ORD record: ord-762beee0dd844d9290c16b34818f5b4b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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