Triethylamine → HCID 69835239, compound

HRID 2300656Notes

Reaction equation

HRID 2300656 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)[O: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[O: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 69835826HCID 69835826, compound

Product 1

HCID 69835239HCID 69835239, 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 98 mg (0.27 mmol) of Intermediate 61, 62 mg (0.27 mmol) of Intermediate 24, and 0.08 mL triethylamine in MeOH (2.0 mL) and trimethylorthoformate (0.5 mL) to yield 95 mg (61% yield) of Example 75 after silica gel chromatography (5%-15% MeOH in DCM): TLC (DCM/MeOH, 4/1): Rf=0.59; 1H NMR (DMSO-d6, 300 MHz) δ11.55 (d, 1H, J=9.0), 7.98-7.90 (m, 4H), 7.73 (d, 2H, J=8.4), 7.51-7.48 (m, 3H), 7.17 (d, 2H, J=8.4), 6.91 (d, 2H, J=8.4), 5.61 (s, 1H), 4.93 (s, 2H), 4.24-4.18 (m, 1H), 3.23-3.16 (m, 1H), 2.86-2.73 (m, 4H), 1.72 (s, 3H), 1.17 (t, 3H, J=7.5); low resolution MS (ES+)m/e 579.05 (MH+).

Sources & evidence

ORD record
ord-c41057885cdb4e96ada8c9883ecd6299
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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