Triethylamine → 4-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]benzene-1,3-diol

HRID 731993

Reaction equation

HRID 731993 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]([O:12]C)[CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[O:6].COC1C=C(OC)C=CC=1C(Cl)=O.F[C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH:41](N)[CH3:42].C(N(CC)CC)C>>[F:34][C:32]1[CH:33]=[CH:28][C:29]2[C:35]3[C:36]([CH:41]([CH3:42])[N:7]([C:5]([C:4]4[CH:8]=[CH:9][C:10]([OH:12])=[CH:11][C:3]=4[OH:2])=[O:6])[C:30]=2[CH:31]=1)=[CH:37][CH:38]=[CH:39][CH:40]=3

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 2390252,4-DimethoxybenzamideHCID 27347192,4-Dimethoxybenzoyl chlorideHCID 224823761-[2-(2,4-Difluorophenyl)phenyl]ethan-1-amine

Product 1

HCID 115303814-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]benzene-1,3-diol

Procedure

N-1-(2′,4′-difluoro-1,1′-biphenyl-2-yl)ethyl]-2,4-dimethoxybenzamide—The title compound was prepared from 2,4-dimethoxybenzoyl chloride (860 mg, 4.28 mmol), 1-(-2′,4′-difluoro-biphenyl-2-yl)-ethylamine (1 g, 4.28 mmol), and triethylamine (717 uL, 5.1 mmol) according to the procedure and in the same manner as described in Example 33, step c resulting in the isolation of 1.47 g (86%) of a white solid. mp 134.8-135.2° C.; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (d, J=5.95 Hz, 3 H) 3.81 (s, 3 H) 3.92 (s, 3 H) 4.93 (d, J=6.73 Hz, 1 H) 6.59 (dd, J=8.79, 2.33 Hz, 1 H) 6.64 (d, J=2.33 Hz, 1 H) 7.18 (m, 2 H) 7.49 (m, 6 H) 8.29 (s, 1 H); MS (ESI) m/z 398 ([M+H]+); Anal. calcd for C23H21F2NO3: C:69.51 H:5.33 N:3.52 Found: C:69.27 H:5.30 N:3.39

Sources & evidence

ORD record
ord-735f84c9216044bca75ffe5b045aab5f
Source dataset
uspto-grants-2009_09
Patent number
US07585871B2

Linked notes

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