Ethyl isocyanate → HCID 58677519, compound

HRID 1012623Notes

Reaction equation

HRID 1012623 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:29]=[C:30]=[O:31])[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:30]([NH:29][CH2:27][CH3:28])=[O:31])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677519HCID 58677519, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 494 (0.04 g, 0.11 mmol) was dissolved in 1,4-dioxan (0.5 mL) and ethyl isocyanate (0.013 mL, 0.16 mmol) was added. The solution was stirred at room temperature 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) 30:70→100:0 as the eluent. This afforded the title compound as an amorphous compound. 13C NMR (DMSO-d6) δ 195.6, 159.0 (dd), 156.0 (dd), 155.3, 149.2, 139.3, 138.3, 133.7, 133.5, 131.5, 129.2, 127.5, 126.4 (dd), 124.5 (dd), 120.2, 118.4, 115.1, 112.1 (dd), 112.0, 105.1 (dd), 34.0, 19.1, 15.4

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-9f18149cdf184377be639a4886bf7a4d
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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