Water → HCID 58677504, compound

HRID 1012613Notes

Reaction equation

HRID 1012613 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.[CH3:27][C:28](=[CH2:37])[C:29]([O:31][CH2:32][CH2:33][N:34]=[C:35]=[O:36])=[O:30].O>N1C=CC=CC=1>[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:35](=[O:36])[NH:34][CH2:33][CH2:32][O:31][C:29](=[O:30])[C:28]([CH3:37])=[CH2:27])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 354092-Isocyanatoethyl methacrylateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677504HCID 58677504, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 494 (0.055 g, 0.15 mmol) was dissolved in dry pyridine (0.3 mL) and isocyanatoethyl methylacrylate (0.031 mL, 0.22 mmol) was added. The solution was stirred at room temperature for 1 h. H2O was added and the water phase was extracted with EtOAc (×2). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 2:1 as the eluent. This afforded the title compound as oil. 13C NMR (CDCl3) δ 196.5, 167.5, 159.2 (dd), 155.8, 155.6 (dd), 148.2, 139.7, 136.3, 135.9, 135.1, 133.9, 132.4, 132.0, 128.6, 126.1, 124.5 (dd), 124.2 (dd), 123.3, 121.2, 116.3, 112.7, 111.6 (dd), 104.9 (dd), 63.9, 39.3, 19.6, 18.2

Workup

  1. extractionthe water phase was extracted with EtOAc (×2)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-1e13af1e0d9c4fe4a0a7f596ddaab737
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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