Phenyl isocyanate → HCID 58677581, compound

HRID 1012624Notes

Reaction equation

HRID 1012624 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]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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:34]([NH:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:35])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677581HCID 58677581, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Compound 494 (0.03 g, 0.08 mmol) was dissolved in 1,4-dioxan (0.5 mL) and phenyl isocyanate (0.013 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 an amorphous compound. 13C NMR (DMSO-d6) δ 195.1, 158.7 (dd), 155.7 (dd), 152.3, 148.9, 139.3, 139.1, 137.2, 133.4, 131.5, 129.6, 128.7, 127.0, 126.2 (dd), 124.2 (dd), 121.8, 120.3, 118.4, 118.2, 118.1, 114.8, 111.9 (dd), 111.8, 105.0 (dd), 19.0

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-098bf3663cce4991ba8476924d917a0d
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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