Water → 1-(2,6-dichlorophenyl)-3-{1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-3-t-butyl-1H-pyrazol-5-yl}urea

HRID 251434Notes

Reaction equation

HRID 251434 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:14]=[C:13]([C:29]([F:32])([F:31])[F:30])[N:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=1[N:41]=[C:42]=[O:43].C(N(CC)CC)C.O>ClCCl>[Cl:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=1[NH:41][C:42]([NH:10][C:8]1[N:7]([C:11]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:14]=[C:13]([C:29]([F:30])([F:32])[F:31])[N:12]=2)[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:9]=1)=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 249626813-t-butyl-1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-1H-pyrazol-5-amine

Product 1

HCID 249575441-(2,6-dichlorophenyl)-3-{1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-3-t-butyl-1H-pyrazol-5-yl}urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 3-t-butyl-1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-1H-pyrazol-5-amine (0.23 mmol) in dichloromethane (3 ml) was treated with 2,6-dichlorophenyl isocyanate (0.056 g, 0.3 mmol) in the presence of triethylamine (0.05 ml), and the reaction was mixture was stirred at room temperature, overnight. Subsequently water (15 ml) was added to above and it was extracted with ethyl acetate (25 ml). The organic layer was evaporated and the crude material purified by column chromatography; elution with 1.5% of ethyl acetate in hexane yielded the title compound. 1H-NMR (CDCl3) δ: 0.86 (s, 9H), 6.58 (s, 1H), 7.02-7.05 (m, 3H), 7.14 (d, 2H), 7.24-7.33 (m, 8H), 8.43-8.44 (br, 1H, D2O exchangeable), 10.52 (br, 1H, D2O exchangeable). MS m/z: 625 (M+).

Workup

  1. extractionwas extracted with ethyl acetate (25 ml)
  2. customThe organic layer was evaporated
  3. customthe crude material purified by column chromatography
  4. washelution with 1.5% of ethyl acetate in hexane

Sources & evidence

ORD record
ord-4f5e583a017741a8a6a3d610f8809327
Source dataset
uspto-grants-2011_01
Patent number
US07863446B2

Reaction notes

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