Acetonitrile → HCID 90404651, compound

HRID 924254Notes

Reaction equation

HRID 924254 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]([NH:14][C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:29]=[CH:28][N:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)[N:26]=2)=[CH:21][CH:20]=1)=[O:16])=[S:13])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].Cl[CH2:47][C:48](=O)[CH3:49].C(#N)C>[Cl-].[Na+].O.ClCCl>[CH:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:48]([CH3:49])=[CH:47][S:13]/[C:12]/1=[N:14]\[C:15]([NH:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[N:29]=[CH:28][N:27]([C:30]3[CH:31]=[CH:32][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:34][CH:35]=3)[N:26]=2)=[CH:23][CH:24]=1)=[O:16])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6571ChloroacetoneHCID 517045Sodium AcetateHCID 90404178HCID 90404178, compound

Product 1

HCID 90404651HCID 90404651, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

To a 20 mL vial was added 1-[(2-isopropyl-4-methyl-phenyl)carbamothioyl]-3-[[4-[1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]methyl]urea (PC5) (0.044 g, 0.077 mmol), sodium acetate (0.019 g, 0.23 mmol), 1-chloropropan-2-one (0.0092 mL, 0.12 mmol) and acetonitrile (1.5 mL). The vial was sealed and 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 an off-white solid (0.010 g, 21%): 1H NMR (400 MHz, DMSO-d6) δ 9.38 (s, 1H), 8.14-8.01 (m, 4H), 7.70 (s, 1H), 7.62 (dq, J=7.7, 1.0 Hz, 2H), 7.45-7.35 (m, 2H), 7.34-7.27 (m, 1H), 7.15 (t, J=1.3 Hz, 2H), 6.66 (q, J=0.9 Hz, 1H), 4.47-4.28 (m, 2H), 2.73-2.62 (m, 1H), 2.39 (s, 3H), 2.10 (d, J=1.1 Hz, 3H), 1.10 (d, J=6.8 Hz, 3H), 1.00 (d, J=6.8 Hz, 3H); 19F NMR (376 MHz, DMSO-d6) δ −56.96; ESIMS m/z 607 ([M+H]+).

Workup

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

Sources & evidence

ORD record
ord-6ec600e593bb47358be5764f79a909d9
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

Loading…