Cyclohexyl isocyanate → 1-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl]-3-cyclohexyl-urea

HRID 1012620Notes

Reaction equation

HRID 1012620 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])=[O:9])[CH:7]=1.[CH:27]1([N:33]=[C:34]=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>N1C=CC=CC=1>[Cl:25][C:11]1[CH:12]=[C:13]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[CH:14]=[CH:15][C:10]=1[C:8]([C:6]1[CH:7]=[C:2]([NH:1][C:34]([NH:33][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:35])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 111679081-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl]-3-cyclohexyl-urea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 494 (0.07 g, 0.18 mmol) was dissolved in pyridine (0.5 mL) and cyclohexyl isocyanate (0.036 mL, 0.28 mmol) was added. The solution was stirred at room temperature for 18 h. Work up as described in the preparation of compound 259. The crude product was purified by flash chromatography using a gradient of EtOAc/petroleum ether (40-60) 15:85→60:40 as the eluent. This afforded the title compound as a slightly coloured solid. 13C NMR (CD3OD) δ 198.5, 161.0 (dd), 157.9 (dd), 157.4, 151.1, 141.0, 138.9, 136.1, 135.0, 132.7, 132.0, 128.9, 127.4 (dd), 126.0 (dd), 122.5, 120.8, 116.6, 112.9, 112.6 (dd), 105.8 (dd), 49.8, 34.5, 26.7, 26.0, 19.7

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-2487bb03834f4c07ab948baf1f81ab49
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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