Acetonitrile → HCID 90404867, compound

HRID 924253Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:26]=[CH:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=4)[N:23]=3)=[CH:18][CH:17]=2)=[O:13])=[S:10])=[C:4]([CH:38]([CH3:40])[CH3:39])[CH:3]=1.[C:41]([O-])(=[O:43])[CH3:42].[Na+].BrCC(OC)=O.C(#N)C>[Cl-].[Na+].O.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:41](=[O:43])[CH2:42][S:10]/[C:9]/2=[N:11]\[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:26]=[CH:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=4)[N:23]=3)=[CH:18][CH:17]=2)=[O:13])=[C:4]([CH:38]([CH3:40])[CH3:39])[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a 20 mL vial was added 1-[(4-fluoro-2-isopropyl-phenyl)carbamothioyl]-3-[[4-[1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]methyl]urea (PC3) (0.092 g, 0.16 mmol), sodium acetate (0.040 g, 0.48 mmol), methyl 2-bromoacetate (0.084 mL, 0.80 mmol) and acetonitrile (2.0 mL). The vial was sealed and the reaction was heated overnight at 65° C. The reaction mixture was diluted with brine solution and dichloromethane and passed through a phase separator. The organic layer was concentrated and the resulting residue was purified by flash column chromatography using 10-80% ethyl acetate/hexanes as eluent providing the title compound as a white solid (0.058 g, 58%).

Workup

customThe vial was sealed
concentrationThe organic layer was concentrated
customthe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-0d3b6f4fc44f4fbb80b1bada8c3908a0
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278964B2

Reaction notes

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