Triethylamine → HCID 69836749, compound

HRID 2300655Notes

Reaction equation

HRID 2300655 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:18][C:19]=2[CH2:20][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.C(N(CC)CC)C>CO.COC(OC)OC.C(Cl)Cl>[CH2:20]([C:19]1[S:18][C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:16][C:15]=1[CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@H:2]([NH:1]/[C:38](/[CH3:39])=[CH:37]\[C:36](=[O:41])[C:33]2[CH:34]=[CH:35][C:30]([C:29]([F:28])([F:42])[F:43])=[CH:31][CH:32]=2)[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1)[CH3:21]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 166409101-(4-(Trifluoromethyl)phenyl)butane-1,3-dioneHCID 69837450HCID 69837450, compound

Product 1

HCID 69836749HCID 69836749, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

The title compound was prepared (as described above for the preparation of Example 2) from 1.35 g (2.72 mmol) of Intermediate 62, 630 mg (2.72 mmol) of Intermediate 24, and 0.8 mL triethylamine in MeOH (20 mL) and trimethylorthoformate (5 mL) to yield 1.04 g (65% yield) of Example 70 after silica gel chromatography (5%-15% MeOH in DCM): TLC (DCM/MeOH, 4/1): Rf=0.45; 1H NMR (DMSO-d6, 300 MHz) δ11.57 (d, 1H, J=8.7), 7.96 (d, 2H, J=8.4), 7.85 (m, 2H), 7.71 (d, 2H, J=8.4), 7.44 (m, 3H), 6.92 (d, 2H, J=8.4), 5.6 (s, 1H), 5.05 (s, 2H), 4.21-4.27 (m, 1H), 3.27-3.22 (m, 1H), 2.89-2.81 (m, 4H), 1.72 (s, 3H), 1.19 (t, 3H, J=7.5); low resolution MS (ES+)m/e 594.96 (MH+).

Sources & evidence

ORD record
ord-aed30761d30443beadc0ed60e29caff2
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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