1-(4-(Trifluoromethyl)phenyl)butane-1,3-dione → HCID 9851511, compound

HRID 2300628Notes

Reaction equation

HRID 2300628 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[F:28][C:29]([F:43])([F:42])[C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:41])[CH2:37][C:38](=O)[CH3:39])=[CH:32][CH:31]=1>>[CH3:39]/[C:38](/[NH:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4])=[CH:37]/[C:36](=[O:41])[C:33]1[CH:34]=[CH:35][C:30]([C:29]([F:28])([F:42])[F:43])=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 166409101-(4-(Trifluoromethyl)phenyl)butane-1,3-dioneHCID 18343041HCID 18343041, compound

Product 1

HCID 9851511HCID 9851511, compound

Procedure

The title compound was prepared (as described above for the preparation of Example 2) from 290 mg (0.76 mmol) of Intermediate 47 and 150 mg (0.76 mmol) of Intermediate 24 to yield 140 mg (31% yield) of Example 10: TLC (DCM/MeOH, 4/1): Rf=0.47; 1H NMR (DMSO-d6, 300 MHz) δ11.52 (d, 1H, J=8.9), 7.96 (d, 2H, J=8.1), 7.80 (m, 2H), 7.72 (d, 2H, J=8.4 ), 7.42 (m, 3H), 7.10 (d, 2H, J=8.4), 6.80 (d, 2H, J=8.4), 5.61 (s, 1H), 4.20 (t, 2H, J=6.6), 4.15 (m, 1H), 3.17 (m, 1H), 3.05 (t, 2H, J=6.5), 2.77 (dd, 1H, J=13.6, 8.6), 2.41 (s, 3H), 1.69 (s, 3H); low resolution MS (ES+)m/e 595.0 (MH+).

Sources & evidence

ORD record
ord-f482c68b7863469e85e8616ef01ee40a
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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