Diisopropylethylamine → HCID 178480222, compound

HRID 706060Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11](=[S:14])[NH:12][CH:13]=2)[CH:4]=[N:3]1.I[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][C:22]2[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][S:14][C:11]3[NH:12][CH:13]=[C:8]([CH2:7][C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)[C:9](=[O:15])[N:10]=3)=[CH:20][CH:21]=2)=[CH:27][C:28]=1[C:33]([F:34])([F:35])[F:36]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-[(1-methyl-1H-pyrazol-4-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (98 mg, 0.442 mmol), 4-chloro-3-(trifluoromethyl)phenyl 4-(2-iodoethyl) phenyl ether (157 mg, 0.368 mmol) and DIPEA (0.193 mL, 1.104 mmol) in chloroform (2 mL) was heated with a microwave reactor at 120° C. for 0.5 h. Purification via reverse phase flash chromatography then afforded the title compound (42 mg, 21.91% yield). LCMS: rt=3.63 min, [M+H+]=521

Workup

customPurification via reverse phase flash chromatography

Sources & evidence

ORD record: ord-5fe1662be63b47daa071a626f459cc7c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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