Triethylamine → HCID 69835843, compound

HRID 2300657Notes

Reaction equation

HRID 2300657 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][C:25]([F:28])=[CH:24][CH:23]=3)[O:18][C:19]=2[CH2:20][CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[F:29][C:30]([F:44])([F:43])[C:31]1[CH:36]=[CH:35][C:34]([C:37](=[O:42])[CH2:38][C:39](=O)[CH3:40])=[CH:33][CH:32]=1.C(N(CC)CC)C>CO.COC(OC)OC.C(Cl)Cl>[CH2:20]([C:19]1[O:18][C:17]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=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:39](/[CH3:40])=[CH:38]\[C:37](=[O:42])[C:34]2[CH:35]=[CH:36][C:31]([C:30]([F:29])([F:43])[F:44])=[CH:32][CH:33]=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 18343042HCID 18343042, compound

Product 1

HCID 69835843HCID 69835843, 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 176 mg (0.46 mmol) of Intermediate 63, 105 mg (0.46 mmol) of Intermediate 24, and 0.14 mL triethylamine in MeOH (3.0 mL) and trimethylorthoformate (0.75 mL) to yield 152 mg (56% yield) of Example 76 after silica gel chromatography (5%-15% MeOH in DCM): TLC (DCM/MeOH, 4/1): Rf=0.55; 1H NMR (DMSO-d6, 300 MHz) δ11.55 (d, 1H, J=9.0), 7.99-7.94 (m, 4H), 7.73 (d, 2H, J=8.4), 7.33 (t, 2H, J=8.7), 7.16 (d, 2H), J=8.4), 6.90 (d, 2H, J=8.7), 5.61 (s, 1H), 4.93 (s, 2H), 4.23-4.18 (m, 1H), 3.22-3.18 (m, 1H), 2.85-2.73 (m, 4H), 1.72 (s, 3H), 1.17 (t, 3H, J=7.5); low resolution MS (ES+)m/e 597.09 (MH+).

Sources & evidence

ORD record
ord-77b77ecbda424de8bd801030a0c6fa61
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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