2,4,6-Trifluorobenzoyl chloride → HCID 69350718, compound

HRID 970740Notes

Reaction equation

HRID 970740 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4]([Cl:6])=[O:5].[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:6].[CH3:13][N:14]([CH3:28])[CH:15]1[CH2:20][CH2:19][C:18]([C:21]2[CH:22]=[C:23]([NH:27][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][C:9]([F:11])=[CH:8][C:7]=3[F:12])[CH:24]=[CH:25][CH:26]=2)=[CH:17][CH2:16]1

Participants

3

Reactant 2

HCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 58852355HCID 58852355, compound

Product 1

HCID 69350718HCID 69350718, compoundYield 85%

Procedure

Using a method similar to example 1, using 2,4,6-trifluorobenzoyl chloride (105 mg, 0.54 mmol) and chiral 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (enantiomer 2, preparation 3, 97 mg, 0.45 mmol) provides of the free base of the title compound (free base 142 mg, 85%): Free base: MS (ES): m/z=375.2 (M+H)+; 1H NMR (CDCl3): δ 7.80 (s, br, 1H), 7.66 (t, 1H), 7.48 (d, 1H), 7.32 (t, 1H), 7.21 (dt, 1H), 6.78 (m 2H), 6.12 (m, 1H), 2.54 (m, 4H), 2.37 (s, 6H), 2.14 (m, 2H), 1.57 (m, 1H). Hydrochloride salt: Anal. cal'd for C21H21F3N2O.HCl.1.2H2O: C, 58.32; H, 5.69; N, 6.48. Found: C, 58.21; H, 5.03; N, 6.39.

Sources & evidence

ORD record
ord-a062f3deabab48a684982d1fa5db6960
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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