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

HRID 726707Notes

Reaction equation

HRID 726707 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=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:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=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 43213212-(3-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 86751967methyl (Z)-[4,4-difluoro-1-[4-[2-(3methylphenyl)benzoylamino]benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetateYield 90.9%

Procedure

Using 277 mg of 2-(3-methylphenyl)benzoic acid, 0.127 ml of oxalyl chloride and 180 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 249 mg of methyl (Z)-[4,4-difluoro-1-[4-[2-(3methylphenyl)benzoylamino]benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetate.

Sources & evidence

ORD record
ord-969decaf9656472890dbddcf8d6019a2
Source dataset
uspto-grants-1998_01
Patent number
US05710150

Reaction notes

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