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

HRID 1012628Notes

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.[C:27]([C:29]1[CH:30]=[C:31]([N:35]=[C:36]=[O:37])[CH:32]=[CH:33][CH:34]=1)#[N:28]>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:31]2[CH:32]=[CH:33][CH:34]=[C:29]([C:27]#[N:28])[CH:30]=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 3-cyanophenyl isocyanate (0.017 g, 0.12 mmol) was added. The solution was stirred at 50° C. for 24 h. 3-Cyanophenyl isocyanate (0.09 g, 0.06 mmol) was added. The solution was stirred at 50° C. for 24 h. Work up as described in the preparation of compound 259. The crude product was purified by flash chromatography using MeOH/CH2Cl2 1:100 as the eluent. This afforded the title compound as yellow oil. 13C NMR (DMSO-d6) δ 195.1, 158.8 (dd), 155.8 (dd), 152.4, 149.2, 140.5, 139.3, 137.0, 133.5, 131.6, 130.2, 130.1, 126.9, 126.5 (dd), 125.4, 124.3 (dd), 123.0, 121.1, 120.8, 118.9, 118.8, 114.9, 112.0 (dd), 111.9, 111.6, 105.1 (dd), 19.1

Workup

stirringThe solution was stirred at 50° C. for 24 h
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-0c2bc7f90ba743a49eefaa96ac391754
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977387B2

Reaction notes

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