3-Chloro-2,6-difluorobenzoyl chloride → HCID 69350631, compound

HRID 970736Notes

Reaction equation

HRID 970736 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH3:13][N:14]([CH3:28])[CH:15]1[CH2:20][CH2:19][C:18]([C:21]2[CH:22]=[C:23]([NH2:27])[CH:24]=[CH:25][CH:26]=2)=[CH:17][CH2:16]1>>[ClH:1].[Cl:1][C:2]1[C:3]([F:12])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]([NH:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:18]2[CH2:19][CH2:20][CH:15]([N:14]([CH3:28])[CH3:13])[CH2:16][CH:17]=2)[CH:22]=1)=[O:6]

Participants

3

Reactant 2

HCID 27735403-Chloro-2,6-difluorobenzoyl chlorideHCID 58852355HCID 58852355, compound

Product 1

HCID 69350631HCID 69350631, compoundYield 116%

Procedure

Using a method similar to example 1, using 3-chloro-2,6-difluorobenzoyl chloride (142 mg, 0.67 mmol) and 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (preparation 2, 121 mg, 0.56 mmol) provides the title compound (free base 166 mg, 76%). Free base: MS (ES): m/z=391.2 (M+H)+; 1H NMR (CDCl3): δ 7.79 (s, br, 1H), 7.68 (br, 1H), 7.49 (m, 2H), 7.34 (t, 1H), 7.22 (d, 1H), 7.00 (dt, 1H), 6.12 (m, 1H), 2.46 (m, 4H), 2.38 (s, 6H), 2.15 (m, 2H), 1.59 (m, 1H). Hydrochloride salt: Anal. cal'd for C21H21ClF2N2O.HCl 0.25H2O: C, 58.41; H, 5.25; N, 6.49. Found: C, 58.65; H, 5.16; N, 6.51.

Sources & evidence

ORD record
ord-45c7142d6206414088e0d3ffc5137ad3
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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