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

HRID 1012630Notes

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:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][CH:30]=1>O1CCOCC1>[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:32]2[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)=[O:37])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 494 (0.03 g, 0.08 mmol) was dissolved in 1,4-dioxan (0.5 mL) and 4-methoxyphenyl isocyanate (0.016 mL, 0.12 mmol) was added. The solution was stirred at 50° C. for 18 h. Work up as described in the preparation of compound 259. The crude product was purified by flash chromatography using MeOH/CH2Cl2 1:100 the eluent. This afforded the title compound as oil. 13C NMR (DMSO-d6) δ 195.2, 158.8 (dd), 155.8 (dd), 154.6, 152.7, 149.1, 139.2, 137.6, 133.5, 132.5, 131.5, 129.5, 127.0, 126.4 (dd), 124.4 (dd), 120.4, 120.2, 119.9, 118.5, 114.9, 114.0, 112.0 (dd), 111.9, 105.1 (dd), 55.2, 19.1

Workup

customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-1f7ca38743394a06bcc28568af7fed9f
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977387B2

Reaction notes

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