Diisopropylethylamine → HCID 178493047, compound

HRID 415416Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (Method 7, 139 mg), N-(5-methoxy-1H-pyrazol-3-yl)-2-(methylsulfonyl)-6-(trifluoromethyl)pyrimidin-4-amine (Method 45, 265 mg) and DIPEA (0.35 ml) in n-BuOH (5.0 ml) was heated at 90° C. for 6 hours. The solvent was removed under reduced pressure and the residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes) to give the titled compound as solid (16.3 mg). 1H NMR δ 12.11 (s, 1H) 10.47 (s, 1H) 8.86 (s, 2H) 8.29 (s, 1H) 6.27 (s, 1H) 5.30 (s, 1H) 5.13-5.25 (m, 1H) 3.77 (s, 3H) 1.51 (d, 3H); m/z 399.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes)

Sources & evidence

ORD record: ord-ca348be9b7144496a0ed7795a6c6d42e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088784B2

Reaction notes

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