Triethylamine → 4'-({2-[(4,4-Dimethylcyclohexyl)amino]ethyl}oxy)-2'-methyl-3-biphenylcarboxamide trifluoroacetate

HRID 70340

Reaction equation

HRID 70340 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([NH2:26])=[O:25])[CH:19]=2)=[C:14]([CH3:27])[CH:13]=1.[CH3:28][C:29]1([CH3:36])[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.CCN(CC)CC>CO.C(Cl)Cl.CC(O)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:28][C:29]1([CH3:36])[CH2:34][CH2:33][CH:32]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([NH2:26])=[O:25])[CH:19]=3)=[C:14]([CH3:27])[CH:13]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 138166Cyclohexanone, 4,4-dimethyl-HCID 671602804'-[(2-Aminoethyl)oxy]-2'-methyl-3-biphenylcarboxamide trifluoroacetate

Product 1

HCID 671600874'-({2-[(4,4-Dimethylcyclohexyl)amino]ethyl}oxy)-2'-methyl-3-biphenylcarboxamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 21877243DCM MeOH AcOHSolvent

Procedure

To a solution of 4′-[(2-aminoethyl)oxy]-2′-methyl-3-biphenylcarboxamide trifluoroacetate (0.105 g; 0.273 mmol; Intermediate VII-1) and 4,4-dimethylcyclohexanone (0.038 g; 0.30 mmol; Intermediate Step 1 of III-1) in MeOH/CH2Cl2/HOAc (3 mL; 1:1 MeOH/CH2Cl2 with 5% HOAc) was added Et3N (0.040 mL; 0.27 mmol), followed by PS—BH3CN (0.32 g; ca. 4.2 mmol/g; ca. 1.35 mmol BH3CN). The mixture was agitated overnight at rt using an orbital shaker, and the resin was removed by filtration. The filtrate was concentrated in vacuo, and the residue was purified by RP-HPLC (C18 column, MeCN/H2O gradient with TFA additive) affording the title compound as a colorless foam. (LC/MS Method C) 2.24 min, m/z 381 (M+1, freebase).

Workup

  1. customthe resin was removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by RP-HPLC (C18 column, MeCN/H2O gradient with TFA additive)

Sources & evidence

ORD record
ord-a5dcf64383874a12a1b733b784bc3e44
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Linked notes

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