Pivaloyl chloride → HCID 57723209、化合物

HRID 1435531ノート

反応式

HRID 1435531 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([NH:17][C:18](=[O:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([F:16])[CH2:12][CH2:11]1.[CH3:21][C:22]([CH3:27])([CH3:26])[C:23](Cl)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:22]([C:27]1[N:8]([CH2:9][CH:10]2[CH2:11][CH2:12][CH:13]([F:16])[CH2:14][CH2:15]2)[C:7]2[CH:6]=[CH:5][C:4]([NH:17][C:18](=[O:20])[CH3:19])=[CH:3][C:2]=2[N:1]=1)([CH3:26])([CH3:23])[CH3:21]

参加物

5

反応物 2

HCID 62493Pivaloyl chlorideHCID 57723216HCID 57723216、化合物

生成物 1

HCID 57723209HCID 57723209、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

N-(3-Amino-4-{[(4-fluorocyclohexyl)methyl]amino}phenyl)acetamide (300 mg, 1.07 mmol) and DMAP (25 mg, 0.214 mmol) were dissolved in DCM (10 mL). Trimethylacetyl chloride (0.145 mL, 1.18 mmol) was added dropwise and the solution was stirred at rt for 1 h. The solution washed with aqueous NaHCO3 solution, brine and dried over anhydrous MgSO4. The residue was dissolved in 5 mL of AcOH and was heated at 150° C. for 2.5 h using a Personal Chemistry microwave apparatus. The solvent was evaporated. The residue was dissolved in EtOAc and washed with aqueous NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography on silica gel using acetone/hexane (2:1) as eluent. Yield: 196 mg (53%). 1H NMR (400 MHz, CDCl3) δ 1.14-1.25 (m, 2 H), 1.37-1.45 (m, 1 H), 1.43-1.51 (m, 1 H), 1.54-1.57 (m, 9 H), 1.70-1.78 (m, 2 H), 1.70-1.77 (m, 1 H), 2.02-2.08 (m, 1 H), 2.10-2.17 (m, 1 H), 2.19-2.21 (m, 3 H), 4.12-4.19 (m, 2 H), 4.53-4.90 (m, 1 H), 7.21-7.29 (m, 1 H), 7.30 (s, 1 H), 7.50-7.57 (m, 1 H), 7.64-7.67 (m, 1 H).

後処理

  1. washThe solution washed with aqueous NaHCO3 solution, brine
  2. dry with materialdried over anhydrous MgSO4
  3. dissolutionThe residue was dissolved in 5 mL of AcOH
  4. temperaturewas heated at 150° C. for 2.5 h
  5. customThe solvent was evaporated
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with aqueous NaHCO3 solution, brine
  8. dry with materialdried over anhydrous MgSO4
  9. customThe crude product was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-cd8e807078ff4bf2ae600830d53bb248
出典データセット
uspto-grants-2009_11
特許番号
US07615642B2

反応ノート

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