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

HRID 471873

반응식

HRID 471873 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21877243DCM MeOH AcOH용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4ab984e802d640959cccafbec10aac60
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633175B2

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