Diisopropylethylamine → HCID 68487422, compound

HRID 1641388Notes

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

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 2,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 7; 0.15 g, 0.553 mmol), (S)-1-(5-bromopyridin-2-yl)ethanamine (Method 26; 0.245 g, 0.611 mmol), and DIEA (0.145 ml, 0.833 mmol) in n-BuOH (2 ml) was heated in a sealed tube at 180° C. in a microwave for 1 hour. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:EtOAc=1:1) to give the title compound as a white solid (0.165 g, 68%). 1H NMR (400 MHz) δ 12.48, 12.38 and 12.07 (s, 1H), 9.66 (br s, 1H), 8.62 (s, 1H), 8.33 and 7.57 (br s, 1H), 7.96 (d, J=8.2 Hz, 1H), 7.92 (br s, 1H), 7.32 (br s, 1H), 5.81 (bs, 1H), 4.99 (br s, 1H), 1.84 (br s, 1H), 1.45 (d, J=6.8 Hz, 3H), 0.94 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 435. Found: [M+11]+ 436.

Workup

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

Sources & evidence

ORD record: ord-33d366dc3e95415e8d3498d47e8a2695
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114989B2

Reaction notes

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