Triethylamine → HCID 67486201, compound

HRID 1880578Notes

Reaction equation

HRID 1880578 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:16][CH2:17][C:18]3[CH:35]=[CH:34][C:21]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:23])=[CH:20][CH:19]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[F:36][C:37]([F:49])([F:48])[O:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:42]3[CH:41]=[CH:40][C:39]([O:38][C:37]([F:36])([F:48])[F:49])=[CH:44][CH:43]=3)=[C:11]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])=[O:23])=[CH:34][CH:35]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 69308245HCID 69308245, compound

Product 1

HCID 67486201HCID 67486201, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A DCM solution (1 mL) containing the intermediate from Step A (22 mg, 0.043 mmol), copper(II) acetate (8 mg, 0.043 mmol), 4-(trifluoromethoxy)phenyl boronic acid (18 mg, 0.086 mmol), triethylamine (0.03 mL, 0.215 mmol) and 4 Å molecular sieves (small spatula tip) was stirred under an air atmosphere. After stirring overnight the solution was filtered and concentrated to give tert-butyl N-[4-(2-{3′,4′-dichloro-4-[4-(trifluoromethoxy)phenoxy]biphenyl-3-yl}ethyl)benzoyl]-β-alaninate. LCMS1 4.85 min. (M+H)=674. The tert butyl group was cleaved as described in EXAMPLE 1 Step I to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.65 (d, J=8.2 Hz, 2H); 7.59 (d, J=2.2 Hz, 1H); 7.51 (d, J=8.3 Hz, 1H); 7.37-7.34 (m, 3H); 7.24 (d, J=8.3 Hz, 2H); 7.21 (d, J=8.4 Hz, 2H); 6.98-6.95 (m, 4H); 3.79 (q, J=5.9 Hz, 2H); 3.01 (s, 4H); 2.80 (t, J=5.8 Hz, 2H). LCMS1 4.43 min. (M+H)=618.

Workup

  1. stirringAfter stirring overnight the solution
  2. filtrationwas filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3d2044fed19d4ec58e631559c0f3149d
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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