Isopropyl isocyanate → HCID 58677553, compound

HRID 1012629Notes

Reaction equation

HRID 1012629 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.[CH:27]([N:30]=[C:31]=[O:32])([CH3:29])[CH3:28]>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:31]([NH:30][CH:27]([CH3:29])[CH3:28])=[O:32])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanate2×HCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677553HCID 58677553, 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 isopropyl isocyanate (0.012 mL, 0.12 mmol) was added. The solution was stirred at 50° C. for 24 h. Isopropyl isocyanate (0.006 mL, 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 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 198.4, 160.9 (dd), 157.8 (dd), 157.4, 151.1, 140.9, 138.7, 136.1, 134.9, 132.6, 131.9, 128.7, 127.3 (dd), 125.9 (dd), 122.4, 120.7, 116.6, 112.9, 112.6 (dd), 105.7 (dd), 42.8, 23.4, 19.6

Workup

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

Sources & evidence

ORD record
ord-8c9ec022eaa344bd96dafffd1a9f736d
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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