Pivaloyl chloride → HCID 57723209, 화합물

HRID 1435531노트

반응식

HRID 1435531 반응식
[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]

참가 물질

5

반응물 2

HCID 62493Pivaloyl chlorideHCID 57723216HCID 57723216, 화합물

생성물 1

HCID 57723209HCID 57723209, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cd8e807078ff4bf2ae600830d53bb248
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615642B2

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