Ethyl isocyanatoacetate → HCID 58677609, compound

HRID 1012615Notes

Reaction equation

HRID 1012615 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.[N:27]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:28]=[O:29]>N1C=CC=CC=1>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][NH:27][C:28]([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:29])[CH3:35]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677609HCID 58677609, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 494 (0.047 g, 0.13 mmol) was dissolved in pyridine (0.3 mL) and ethyl isocyanatoacetate (0.022 mL, 0.19 mmol) was added. The solution was stirred at room temperature for 2 h. Work up as described in the preparation of compound 259. The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 1:1 as the eluent. This afforded the title compound as a slightly coloured solid. 13C NMR (DMSO-d6) δ 195.2, 170.7, 158.7 (dd), 155.7 (dd), 155.0, 149.0, 139.0, 137.8, 133.3, 131.4, 129.1, 127.0, 126.3 (dd), 124.3 (dd), 120.0, 118.1, 114.8, 111.9 (dd), 111.8, 105.0 (dd), 60.2, 41.3, 19.0, 14.0

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-791cabd9c34e4e9fb245160cc7e7e68c
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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