Diisopropylethylamine → 2-methyl-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamic acid tert-butyl ester

HRID 2223302Notes

Reaction equation

HRID 2223302 reaction equation
[C:1]([O:5][C:6](=[O:12])[CH:7]([CH3:11])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].[NH2:13][CH:14]1[C:20](=[O:21])[N:19]([CH3:22])[C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=2[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]1=2.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>C1COCC1>[C:1]([O:5][C:6](=[O:12])[CH:7]([CH3:11])[C:8]([NH:13][CH:14]1[C:20](=[O:21])[N:19]([CH3:22])[C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=2[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]1=2)=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 101986267-Amino-5-methyl-5H-dibenzo[b,d]azepin-6(7H)-oneHCID 178517023-(Tert-butoxy)-2-methyl-3-oxopropanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 690397662-methyl-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (0° C.) of 2-methyl-malonic acid mono-tert-butyl ester (1.01 g, 5.79 mmol) and 7-amino-5-methyl-5H,7H-dibenzo[b,d]azepin-6-one (1.15 g, 4.83 mmol) in THF (8 ml) was added hydroxybenzotriazole (652 mg, 4.83 mmol), diisopropylethylamine (624 mg, 4.83 mmol)and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (925 mg, 4.83 mmol), and the mixture was stirred overnight at r.t. The solvent was evaporated, the residue was taken up in ethyl acetate, washed with water, and dried (Na2SO4). After evaporation of the solvent, the title compound, MS: m/e=395.3 (M+H+), (920 mg, 48%) was obtained by chromatographic purification of the residue (silica gel, MeOH, CH2Cl2).

Workup

  1. customThe solvent was evaporated
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-2a2568255a924934a7d158f5823a28b0
Source dataset
uspto-grants-2008_05
Patent number
US07375099B2

Reaction notes

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