Diisopropylethylamine → HCID 118162175, compound

HRID 1749460Notes

Reaction equation

[OH:1][C@H:2]1[CH2:5][C@@H:4]([NH:6][C:7]2[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9](S(C)(=O)=O)[N:8]=2)[C:3]1([CH3:20])[CH3:19].[NH2:21][CH2:22][CH2:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([O:32][C:33]([F:36])([F:35])[F:34])[CH:25]=1.CCN(C(C)C)C(C)C>C1COCC1>[C:28]([C:27]1[CH:30]=[CH:31][C:24]([CH2:23][CH2:22][NH:21][C:9]2[N:8]=[C:7]([NH:6][C@@H:4]3[CH2:5][C@H:2]([OH:1])[C:3]3([CH3:20])[CH3:19])[C:12]([C:13]#[N:14])=[CH:11][N:10]=2)=[CH:25][C:26]=1[O:32][C:33]([F:34])([F:35])[F:36])#[N:29]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(((1R,3S)-3-hydroxy-2,2-dimethylcyclobutyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (80 mg, 0.27 mmol), 4-(2-aminoethyl)-2-(trifluoromethoxy)benzonitrile (60 mg, crude)) and DIEA (105 mg, 0.81 mmol) in THF (2 mL) was stirred at 100° C. in a microwave reactor for 1.5 h. After cooling to room temperature, the reaction mixture was concentrated and the residue purified by standard methods to afford the title compound (34.4 mg, 0.077 mmol, 40% yield, over two steps). 1H NMR (400 MHz, CD3OD) δ8.14-8.07 (m, 1H), 7.82-7.80 (m, 1H), 7.45-7.43 (m, 2H), 3.97-3.93 (m, 1H), 3.83-3.70 (m, 2H), 3.68-3.59 (m, 1H), 3.10-2.01 (m, 2H), 2.58-2.54 (m, 1H), 2.15-2.06 (m, 1H), 1.21 (s, 3H), 0.95 (s, 3H). MS (ESI) m/z 447.2 [M+1]+.

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated
customthe residue purified by standard methods

Sources & evidence

ORD record: ord-f855a2dda5f940faa6fecf417534bbaf
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

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