2-Chloro-4-fluorobenzoyl chloride → HCID 69351039, compound

HRID 970742Notes

Reaction equation

HRID 970742 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:12][N:13]([CH3:27])[CH:14]1[CH2:19][CH2:18][C:17]([C:20]2[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=2)=[CH:16][CH2:15]1>>[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:17]2[CH2:18][CH2:19][CH:14]([N:13]([CH3:27])[CH3:12])[CH2:15][CH:16]=2)[CH:21]=1)=[O:5]

Participants

3

Reactant 2

HCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 58852355HCID 58852355, compound

Product 1

HCID 69351039HCID 69351039, compoundYield 143.9%

Procedure

Using a method similar to example 1, using 2-chloro-4-fluorobenzoyl chloride (106 mg, 0.55 mmol) and 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (enantiomer 2, preparation 3, 99 mg, 0.46 mmol) provides the title compound (free base 162 mg, 94%): MS (ES): m/z=373.2 (M+H)+; 1H NMR (CDCl3): δ 8.04 (s, br, 1H), 7.78 (m, 1H), 7.68 (s, 1H), 7.50 (d, 1H), 7.33 (t, 1H), 7.20 (m, 2H), 7.10 (m, 1H), 6.12 (m, 1H), 2.55 (4H), 2.37 (s, 6H), 2.15 (m, 2H), 1.57 (m, 1H). Hydrochloride salt: Anal. cal'd for C21H22ClFN2O.HCl 0.5H2O: C, 60.29; H, 5.78; N, 6.70. Found: C, 60.11; H, 5.42; N, 6.62.

Sources & evidence

ORD record
ord-f9a3242dea1a46a08409dad548bd8403
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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