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

HRID 1012616Notes

Reaction equation

HRID 1012616 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.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([N:35]=[C:36]=[O:37])[CH:32]=[CH:33][CH:34]=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:36]([NH:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([O:28][CH3:27])[CH:30]=2)=[O:37])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

4

Reactant 2

HCID 878433-Methoxyphenyl isocyanateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 586775151-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-3-(3-methoxy-phenyl)-urea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 494 (0.03 g, 0.08 mmol) was dissolved in pyridine (0.2 mL) and 3-methoxyphenyl isocyanate (0.016 mL, 0.12 mmol) was added. The solution was stirred at room temperature for 1.5 h. Work up as described in the preparation of compound 259. The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 2:3 as the eluent. This afforded the title compound as a slightly coloured solid. 13C NMR (CD3OD) δ 198.3, 161.7, 161.0 (dd), 157.9 (dd), 155.3, 151.2, 141.6, 141.2, 138.3, 136.2, 135.0, 132.7, 132.6, 130.6, 128.7, 127.4 (dd), 126.0 (dd), 122.8, 121.1, 116.7, 113.0, 112.7, 112.6 (dd), 109.5, 106.3, 105.8 (dd), 55.7, 19.7

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c15507f69cde40928943bc7e01f0e704
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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