Diisopropylethylamine → HCID 68158281, compound

HRID 243482Notes

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]([CH:13]([CH3:15])[CH3:14])[C:6]=2[C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[NH2:23][C:24]1[C:29]([C:30]#[N:31])=[C:28](Cl)[N:27]=[CH:26][N:25]=1.CCN(C(C)C)C(C)C>CC(O)C>[NH2:23][C:24]1[C:29]([C:30]#[N:31])=[C:28]([NH:12][C@H:10]([C:8]2[N:7]([CH:13]([CH3:14])[CH3:15])[C:6]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[N:9]=2)[CH3:11])[N:27]=[CH:26][N:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(S)-1-(6-Fluoro-1-isopropyl-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine (0.166 g, 0.56 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (86 mg, 0.56 mmol) and DIPEA (497 μL, 2.78 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 (SiO2, eluting with 0-10% methanol in DCM) to give 408 as a white solid (140 mg, 61%). LCMS (Method K): RT 3.28 min [M+H]+ 417. 1H NMR (DMSO-d6, 400 MHz): δ 8.70 (1H, ddd, J=4.8, 1.7, 0.8 Hz), 7.99 (1H, s), 7.93 (1H, td, J=7.8, 1.8 Hz), 7.67 (1H, dd, J=8.8, 4.9 Hz), 7.61 (1H, d, J=7.6 Hz), 7.48 (1H, ddd, J=7.6, 4.8, 1.2 Hz), 7.29 (3H, br s), 7.12 (1H, dd, J=10.3, 8.8 Hz), 5.64 (1H, sept, J=7.1 Hz), 4.01-3.89 (1H, m), 1.55 (3H, d, J=6.6 Hz), 1.27-1.11 (6H, m)

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe resultant residue purified by flash chromatography (SiO2, eluting with 0-10% methanol in DCM)

Sources & evidence

ORD record: ord-b01d118771434043bbe6e0cd32507c2f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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