Triethylamine → N-allyl-2-bromo-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-methoxybenzamide

HRID 507002Notes

Reaction equation

HRID 507002 reaction equation
[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:8]([NH:10][CH:11]1[CH2:13][CH2:12]1)=[O:9])[CH:2]=[CH2:3].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[C:27](Cl)=[O:28].C(N(CC)CC)C>C1COCC1>[CH2:1]([N:4]([C:5]1[CH:6]=[C:7]([C:8]([NH:10][CH:11]2[CH2:12][CH2:13]2)=[O:9])[CH:14]=[CH:15][C:16]=1[CH3:17])[C:27](=[O:28])[C:20]1[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:19]=1[Br:18])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27816562-Bromo-5-methoxybenzoyl chlorideHCID 670185693-(allylamino)-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 67018660N-allyl-2-bromo-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-methoxybenzamideYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(Allylamino)-N-cyclopropyl-4-methylbenzamide (688 mg) was stirred with 2-bromo-5-methoxybenzene-1-carbonyl chloride (745 mg) and triethylamine (0.83 ml) in THF (10 ml) at room temperature for 2.5 hours and then concentrated. The residue was dissolved in ethyl acetate and washed with 1N HCl (×2), water, brine, dried (magnesium sulfate) and concentrated to yield N-allyl-2-bromo-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-methoxybenzamide as a pale orange solid (1.24 g); Mass Spectrum: M+H+ 443.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1N HCl (×2), water, brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2a2d7090e444c13abbe09c5c7d38e7b
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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