Pyridine → [(cis)-1-Acetyl-6-bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide

HRID 2041719

반응식

HRID 2041719 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C@@H:7]([CH2:12][CH2:13][CH3:14])[CH2:6][C@H:5]2[NH:15][CH:16]=[O:17].[C:18](Cl)(=[O:20])[CH3:19].N1C=CC=CC=1>C(Cl)Cl>[C:18]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[C@H:5]([NH:15][CH:16]=[O:17])[CH2:6][C@@H:7]1[CH2:12][CH2:13][CH3:14])(=[O:20])[CH3:19]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86669448[(cis)-6-Bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide

생성물 1

HCID 86669447[(cis)-1-Acetyl-6-bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

[(cis)-6-Bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide (for a preparation see intermediate 89) (8.0 g, 26.9 mmol) in DCM (100 mL) was added dropwise at room temperature to a mixture of acetyl chloride (6.7 mL, 94.28 mmol) and pyridine (10.85 mL, 134.7 mmol) in DCM (150 mL). The resulting mixture was stirred at this temperature for 1 h then was washed with 1M NaOH aqueous solution, 1M HCl aqueous solution, a saturated NaHCO3 aqueous solution then brine, was dried over MgSO4 and concentrated in vacuovacuo. Purification of the residue by flash chromatography on silica gel (20:1 DCM/MeOH) gave [(cis)-1-acetyl-6-bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide (6.29 g, 18.5 mmol, 68%) as a light orange solid.

후처리

  1. washthen was washed with 1M NaOH aqueous solution, 1M HCl aqueous solution
  2. dry with materiala saturated NaHCO3 aqueous solution then brine, was dried over MgSO4
  3. concentrationconcentrated in vacuovacuo
  4. customPurification of the residue by flash chromatography on silica gel (20:1 DCM/MeOH)

출처 및 근거

ORD 기록
ord-c53f52c985634eee9c41dc773763c218
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580957B2

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