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

HRID 1012625Notes

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.[CH2:27]([N:31]=[C:32]=[O:33])[CH2:28][CH2:29][CH3:30]>O1CCOCC1>[CH2:27]([NH:31][C:32]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8](=[O:9])[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])[CH:7]=1)=[O:33])[CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 494 (0.03 g, 0.08 mmol) was dissolved in 1,4-dioxan (0.5 mL) and n-butyl isocyanate (0.014 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 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), 158.3, 157.9 (dd), 151.1, 141.0, 138.9, 136.1, 135.0, 132.7, 132.1, 128.9, 127.4 (dd), 126.0 (dd), 122.5, 120.9, 116.6, 112.9, 112.6 (dd), 105.8 (dd), 40.6, 33.3, 21.0, 19.7, 14.1

Workup

customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-deeca837f6444b10a872aaf4c0990ffb
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977387B2

Reaction notes

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