Diisopropylethylamine → (R)-N3-Isobutyl-N3,4'-dimethyl-N5-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)biphenyl-3,5-dicarboxamide

HRID 1845165Notes

Reaction equation

HRID 1845165 reaction equation
[CH2:1]([N:5]([CH3:24])[C:6]([C:8]1[CH:9]=[C:10]([C:21](O)=[O:22])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:13]=1)=[O:7])[CH:2]([CH3:4])[CH3:3].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[F:48][C:49]([F:60])([F:59])[C:50]1[N:55]=[CH:54][C:53]([C@H:56]([NH2:58])[CH3:57])=[CH:52][CH:51]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH2:1]([N:5]([CH3:24])[C:6]([C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:11]=[C:10]([C:21]([NH:58][C@@H:56]([C:53]2[CH:54]=[N:55][C:50]([C:49]([F:59])([F:48])[F:60])=[CH:51][CH:52]=2)[CH3:57])=[O:22])[CH:9]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 55278063(1R)-1-[6-(Trifluoromethyl)(3-pyridyl)]ethylamineHCID 581880895-(Isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 58188058(R)-N3-Isobutyl-N3,4'-dimethyl-N5-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)biphenyl-3,5-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(isobutyl(methyl)carbamoyl)-4′-methylbiphenyl-3-carboxylic acid (21 mg, 0.064 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (25 mg, 0.13 mmol), 1-hydroxybenzotriazole hydrate (9.9 mg, 0.064 mmol), and CH2Cl2 (3 mL) were added (R)-1-(6-(trifluoromethyl)pyridin-3-yl)ethanamine (18 mg, 0.097 mmol) (WO 2008/130481) and N,N-diisopropylethylamine (17 μL, 0.097 mmol). The mixture was stirred at room temperature overnight, and then concentrated in vacuo. The residue was purified by preparative HPLC (100×21.2 mm C18 column, 40-80% MeCN/water[10 mM Et2NH]) to afford a white foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, 40-80% MeCN/water[10 mM Et2NH])
  3. customto afford a white foam

Sources & evidence

ORD record
ord-0b89a66a32434fdfb0778da6ff2332a3
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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