6-Fluoro-3,4-dihydro-2H-1-benzopyran-4-carboxylic acid → N-[(4-dimethylaminophenyl)methyl]-6-fluoro-N-(4-isopropylphenyl)chroman-4-carboxamide

HRID 218585Notes

Reaction equation

HRID 218585 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:12]([OH:14])=O.[CH3:15][N:16]([CH3:34])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1>>[CH3:15][N:16]([CH3:34])[C:17]1[CH:18]=[CH:19][C:20]([CH2:23][N:24]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:32])[CH3:33])=[CH:27][CH:26]=2)[C:12]([CH:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=3)[O:8][CH2:7][CH2:6]2)=[O:14])=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 139537996-Fluoro-3,4-dihydro-2H-1-benzopyran-4-carboxylic acidHCID 21957887N-(4-(Dimethylamino)benzyl)-4-isopropylbenzenamine

Product 1

HCID 10182151N-[(4-dimethylaminophenyl)methyl]-6-fluoro-N-(4-isopropylphenyl)chroman-4-carboxamideYield 64.8%

Procedure

By the reaction and treatment in the same manner as in Example 1 using 6-fluorochroman-4-carboxylic acid (1.96 g) and [(4-dimethylaminophenyl)methyl] (4-isopropylphenyl) amine (2.68 g) as starting materials, N-[(4-dimethylaminophenyl)methyl]-6-fluoro-N-(4-isopropylphenyl)chroman-4-carboxamide (2.89 g) was obtained. melting point: 95-98° C.

Sources & evidence

ORD record
ord-2404d6b41e504e96b0614c6a4865d78f
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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