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

HRID 471873Notes

Reaction equation

HRID 471873 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-4ab984e802d640959cccafbec10aac60
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

Loading…