2-Butanone, 3-bromo- → HCID 16743932, compound

HRID 1993612Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@@:12]([NH:27][C:28]([NH2:30])=[S:29])([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Br[CH:32]([CH3:36])[C:33](=O)[CH3:34]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C@@:12]([NH:27][C:28]2[S:29][C:32]([CH3:36])=[C:33]([CH3:34])[N:30]=2)([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The thiourea (28 mg, 0.064 mmol) in ethanol (0.3 mL) in a two drum vial was added 3-bromobutan-2-one (28 mg, 0.18 mmol). The vial was heated in a shaker at 90° C. for 1 hour. The reaction was concentrated and crude mixture was purified by prep HPLC to give the (S)-N-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)4,5-dimethylthiazol-2-amine as a white solid (31 mg, 99% yield). LCMS: 3.63 min [M+1] 498.34 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CDCl3) δ ppm 2.06 (s, 3H), 2.22 (s, 3H), 3.62-3.73 (m, 1H), 3.74-3.85 (m, 1H), 6.57 (d, J=7.58 Hz, 2H), 7.06-7.16 (m, 4H), 7.17-7.23 (m, 2H), 7.24-7.31 (m, 1H), 7.39 (dd, J=8.59, 5.05 Hz, 2H) 11.25(s, 1H).

Workup

concentrationThe reaction was concentrated
customcrude mixture was purified by prep HPLC

Sources & evidence

ORD record: ord-ca35189313304aaab77b9ee8872d2b7e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652023B2

Reaction notes

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