Diisopropylethylamine → HCID 118162092, compound

HRID 1749526Notes

Reaction equation

[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11](SC)[N:10]=2)[C:3]1([CH3:20])[CH3:19].[F:21][C:22]([F:34])([CH3:33])[CH2:23][O:24][C:25]1[C:30]([CH2:31][NH2:32])=[CH:29][N:28]=[CH:27][N:26]=1.CCN(C(C)C)C(C)C>C1COCC1>[F:34][C:22]([F:21])([CH3:33])[CH2:23][O:24][C:25]1[C:30]([CH2:31][NH:32][C:11]2[N:10]=[C:9]([NH:8][C@@H:4]3[CH2:5][CH2:6][CH2:7][C@H:2]([OH:1])[C:3]3([CH3:20])[CH3:19])[C:14]([C:15]#[N:16])=[CH:13][N:12]=2)=[CH:29][N:28]=[CH:27][N:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-(((1R,3S)-3-hydroxy-2,2-dimethylcyclohexyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile (130 mg, crude) in THF (3.0 mL) was added (4-(2,2-difluoropropoxyl)pyrimidin-5-yl)methanamine (84 mg, 0.411 mmol) and DIEA (158 mg, 1.23 mmol). The resulting mixture was stirred at 100° C. in a microwave reactor for 1 h. The solvent was evaporated and the residue was purified by standard methods to afford the title compound (33.6 mg, 0.075 mmol, 20% yield for two steps). 1H NMR (400 MHz, CD3OD) δ (ppm) 8.69 (s, 1H), 8.40 (s, 1H), 8.13 (s, 1H), 4.72 (t, J=12.0 Hz, 2H), 4.57 (s, 2H), 4.05-3.91 (m, 1H), 3.45-3.42 (m, 1H), 1.82-1.72 (m, 5H), 1.70-1.50 (m, 2H), 1.50-1.30 (m, 2H), 1.03-0.91 (m, 6H). MS (ESI) m/z 448.2 [M+H]+.

Workup

customThe solvent was evaporated
customthe residue was purified by standard methods

Sources & evidence

ORD record: ord-7b406244882c455e9a39b3c3a6c7133a
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

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