Ethanesulfonyl chloride → HCID 58677678, compound

HRID 1012612Notes

Reaction equation

HRID 1012612 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]([S:29](Cl)(=[O:31])=[O:30])[CH3:28]>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][S:29]([CH2:27][CH3:28])(=[O:31])=[O:30])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677678HCID 58677678, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 494 (0.045 g, 0.12 mmol) was dissolved in pyridine (0.3 mL). Ethanesulphonyl chloride (0.017 mL, 0.18 mmol) was added and the solution was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo and the oil was dissolved in EtOAc and washed with H2O. The water phase was extracted with EtOAc and the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using a gradient of EtOAc/petroleum ether (40-60) 15:85→40:60 as the eluent. This afforded the title compound as yellow solid. 13C NMR (CDCl3) δ 195.5, 159.3 (dd), 155.7 (dd), 148.3, 140.4, 135.3, 134.5, 134.5, 133.8, 132.5, 128.5, 124.6 (dd), 124.2 (dd), 123.2, 121.6, 116.1, 112.8, 111.6 (dd), 105.0 (dd), 45.9, 19.7, 8.1

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe oil was dissolved in EtOAc
  3. washwashed with H2O
  4. extractionThe water phase was extracted with EtOAc
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-218a0b2d47bf4563a58cf7269f3b9888
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

Loading…