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

HRID 70340

反応式

HRID 70340 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21877243DCM MeOH AcOH溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a5dcf64383874a12a1b733b784bc3e44
出典データセット
uspto-grants-2014_09
特許番号
US08822518B2

関連ノート

読み込み中…