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

HRID 970737Notes

Reaction equation

HRID 970737 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 147.3%

Procedure

Using a method similar to example 1, using 2-chloro-6-fluorobenzoyl chloride (132 mg, 0.69 mmol) and 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (preparation 2, 124 mg, 0.57 mmol) provides the title compound (free base 208 mg, 98%). Free base: MS (ES): m/z=373.2 (M+H)+; 1H NMR (CDCl3): δ 7.68 (m, 2H), 7.52 (d, 1H), 7.36 (m, 2H), 7.25 (m, 1H), 7.23 (t, 1H), 7.10 (m, 1H), 6.12 (m, 1H), 2.50 (m, 4H), 2.36 (s, 6H), 2.15 (m, 2H), 1.58 (m, 1H). Hydrochloride salt: Anal. cal'd for C21H22ClFN2O.HCl 0.6H2O: C, 60.03; H, 5.81; N, 6.67. Found: C, 59.75; H, 5.31; N, 6.55.

Sources & evidence

ORD record
ord-698ac054e90f459ba8929ef426ac86ac
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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