Oxalyl chloride → methyl (Z)-[4,4-difluoro-1-[4-[2-(4methylphenyl)benzoylamino]benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetate

HRID 726706Notes

Reaction equation

HRID 726706 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:23][C:24]1[CH:49]=[CH:48][C:27]([C:28]([N:30]2[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3/[C:34](=[CH:41]/[C:42]([O:44][CH3:45])=[O:43])/[C:33]([F:47])([F:46])[CH2:32][CH2:31]2)=[O:29])=[CH:26][CH:25]=1>>[F:47][C:33]1([F:46])[CH2:32][CH2:31][N:30]([C:28](=[O:29])[C:27]2[CH:26]=[CH:25][C:24]([NH:23][C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[CH:49][CH:48]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2/[C:34]/1=[CH:41]/[C:42]([O:44][CH3:45])=[O:43]

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 815682-(4-Methylphenyl)benzoic acidHCID 10809276methyl (Z)-[1-(4-aminobenzoyl)-4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetate

Product 1

HCID 86751966methyl (Z)-[4,4-difluoro-1-[4-[2-(4methylphenyl)benzoylamino]benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetateYield 54.5%

Procedure

Using 630 mg of 2-(4-methylphenyl)benzoic acid, 0.389 ml of oxalyl chloride and 670 mg of methyl (Z)-[1-(4-aminobenzoyl)-4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetate, a similar procedure as in Reference Example 8 was repeated to obtain 556 mg of methyl (Z)-[4,4-difluoro-1-[4-[2-(4methylphenyl)benzoylamino]benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetate.

Sources & evidence

ORD record
ord-48206d1fc15c4008984b0c67c2c2a8af
Source dataset
uspto-grants-1998_01
Patent number
US05710150

Reaction notes

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