Triethylamine → HCID 69835993, compound

HRID 2300654Notes

Reaction equation

HRID 2300654 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:20][C:21]=2[CH2:22][CH3:23])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[F:30][C:31]([F:45])([F:44])[C:32]1[CH:37]=[CH:36][C:35]([C:38](=[O:43])[CH2:39][C:40](=O)[CH3:41])=[CH:34][CH:33]=1.C(N(CC)CC)C>CO.COC(OC)OC.C(Cl)Cl>[CH2:22]([C:21]1[O:20][C:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:18][C:17]=1[CH2:16][CH2:15][CH2:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C@H:2]([NH:1]/[C:40](/[CH3:41])=[CH:39]\[C:38](=[O:43])[C:35]2[CH:36]=[CH:37][C:32]([C:31]([F:30])([F:44])[F:45])=[CH:33][CH:34]=2)[C:3]([OH:5])=[O:4])=[CH:8][CH:9]=1)[CH3:23]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 166409101-(4-(Trifluoromethyl)phenyl)butane-1,3-dioneHCID 57098989HCID 57098989, compound

Product 1

HCID 69835993HCID 69835993, 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 57 mg (0.14 mmol) of Intermediate 60, 33 mg (0.14 mmol) of Intermediate 24, and 0.042 mL triethylamine in MeOH (1.5 mL) and trimethylorthoformate (0.5 mL) to yield 24 mg (28% yield) of Example 67 after silica gel chromatography (5%-15% MeOH in DCM): TLC (DCM/MeOH, 4/1): Rf=0.62; 1H NMR (DMSO-d6, 300 MHz) δ11.53 (d,1H, J=9.0), 7.97 (d, 2H, J=8.4), 7.89 (d, 2H, J=7.8), 7.73 (d, 2H, J=8.4), 7.46 (m, 3H), 7.97 (d, 2H, J=8.1), 6.79 (d, 2H, J=8.4), 5.62 (s, 1H), 4.25-4.19 (m, 1H), 3.90 (t, 2H, J=6.0), 3.21-3.15 (m, 1H), 2.58-2.83 (m, 5H), 1.98 (t, 2H, J=5.7), 1.72 (s, 3H), 1.11 (t, 3H, J=7.5); low resolution MS (ES+)m/e 607.18 (MH+).

Sources & evidence

ORD record
ord-86d29139198a4f3f956c2cc7184c8ef3
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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