2-Ethylpropanedioyl dichloride → 3-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-3-oxo-propionamide

HRID 346450

Reaction equation

HRID 346450 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])C.Cl.FC1C=C(C=CC=1)COC1C=CC2CC[NH:42]CCC=2C=1.C(C(C(Cl)=O)C(Cl)=O)C>C(N(CC)CC)C>[F:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][N:8]([C:6](=[O:7])[CH2:5][C:4]([NH2:42])=[O:3])[CH2:14][CH2:13][C:12]=2[CH:15]=1

Participants

5

Reactant 3

HCID 109209242-Ethylpropanedioyl dichlorideHCID 210801847-(3-fluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochlorideHCID 69290734HCID 69290734, compound

Product 1

HCID 117726833-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-3-oxo-propionamideYield 70%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-3-oxo-propionic acid ethyl ester: The title compound was prepared in analogy to Example 1d) from 7-(3-fluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [Example 1c)] and ethyl malonic acid chloride with triethylamine as the base. Yield: 70% of theory as a colourless oil; MS: m/e=386 (M+H)+.

Sources & evidence

ORD record
ord-0cc9c9d9b5fb4a71ae071e7b3c235fb3
Source dataset
uspto-grants-2007_02
Patent number
US07173023B2

Linked notes

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