Water → HCID 68574450, compound

HRID 1949065Notes

Reaction equation

HRID 1949065 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[CH:7]=[CH:6]2.C(N(CC)CC)C.[F:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1.O>C1COCC1>[F:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:1][CH2:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH:7]=[CH:6]3)=[O:36])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 68574969HCID 68574969, compound

Product 1

HCID 68574450HCID 68574450, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (ice bath) and stirred solution of (6-aminomethyl-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.68 mmol) and triethyl amine (75 mg, 0.76 mmol) in THF (4 ml) was added 4-fluorobenzoyl chloride (119 mg, 0.75 mmol) and the mixture was allowed to stir at room temperature for 16 h. The reaction mixture was poured into water (15 ml) and extracted with diethyl acetate (2×20 ml). The combined organic layers were washed with brine (1×20 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/hexane) to yield the title compound as white foam (250 mg, 88%).

Workup

  1. temperatureTo a cooled (ice bath)
  2. extractionextracted with diethyl acetate (2×20 ml)
  3. washThe combined organic layers were washed with brine (1×20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/hexane)

Sources & evidence

ORD record
ord-52e70b10ebed44619c9eebf01f58d3f4
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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