Diisopropylethylamine → HCID 16097529, compound

HRID 1641387Notes

Reaction equation

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

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of 2,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 7; 0.18 g, 0.666 mmol), (S)-1-(3,5-difluoropyridin-2-yl)ethanamine (Method 21; 0.132 g, 0.833 mmol), and DIEA (0.139 ml, 0.800 mmol) in n-BuOH (2 ml) was heated in a sealed tube at 175° C. for 17 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:EtOAc=1.5:1) to give the title compound as a white solid (0.21 g, 80%). 1H NMR (400 MHz) δ 12.50 and 12.09 (s, 1H), 9.60 and 8.50 (s, 1H), 8.43 and 8.35 (s, 1H), 7.88-8.04 (m, 3H), 7.26 (br, 1H), 5.33 (m, 1H), 1.88 (m, 1H), 1.36 (d, J=6.8 Hz, 3H), 0.94 (m, 1H), 0.86 (m, 1H), 0.74 (m, 1H), 0.62 (m, 1H). MS: Calcd.: 391. Found: [M+H]+ 392.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (hexane:EtOAc=1.5:1)

Sources & evidence

ORD record: ord-7323a0d1ee624732828309e259214e53
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114989B2

Reaction notes

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