2-Chloro-6-fluorobenzoyl chloride → HCID 69351422, compound

HRID 970741Notes

Reaction equation

HRID 970741 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[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]=[CH:9][CH:8]=[C:7]([F:11])[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 27365472-Chloro-6-fluorobenzoyl chlorideHCID 58852355HCID 58852355, compound

Product 1

HCID 69351422HCID 69351422, compoundYield 138.3%

Procedure

Using a method similar to example 1, using 2-chloro-6-fluorobenzoyl chloride (103 mg, 0.53 mmol) and 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (enantiomer 2, preparation 3, 96 mg, 0.44 mmol) provides the title compound (free base 150 mg, 91%): Free base: MS (ES): m/z=373.1 (M+H)+; 1H NMR (CDCl3): δ7.90 (s, 1H), 7.67 (t, 1H), 7.52 (d, 1H), 7.27 (m, 4H), 7.08 (m, 1H), 6.10 (m, 1H), 2.52 (m, 4H), 2.34 (s, 6H), 2.12 (m, 2H), 1.55 (m, 1H). Hydrochloride salt: Anal. cal'd for C21H22ClFN2O.HCl0.25H2O: C, 60.95; H, 5.72; N, 6.77. Found: C, 60.81; H, 5.57; N, 6.81.

Sources & evidence

ORD record
ord-b5caf2299a1d4cf9bd61bac7ab7cc950
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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