Propionic Acid → HCID 71811363、化合物

HRID 714066ノート

反応式

HRID 714066 の反応式
[NH2:1][CH:2]1[C:11]2[CH:10]=[N:9][CH:8]=[C:7]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[C:20](O)(=[O:23])[CH2:21][CH3:22].CCN=C=NCCCN(C)C.OP([O-])(O)=O.[K+]>C(Cl)Cl>[C:16]([C:15]1[CH:14]=[CH:13][C:12]([C:7]2[C:6]3[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][C:20](=[O:23])[CH2:21][CH3:22])[C:11]=3[CH:10]=[N:9][CH:8]=2)=[CH:19][CH:18]=1)#[N:17]

参加物

6

反応物 4

HCID 1032Propionic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516951Monobasic potassium phosphateHCID 718113604-(8-Amino-5,6,7,8-tetrahydro-4-isoquinolinyl)benzonitrile

生成物 1

HCID 71811363HCID 71811363、化合物収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (rac)-4-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile (example 1) (480 mg, 1.93 mmol) and propionic acid (158 μL, 2.12 mmol) in CH2Cl2 (10 mL) at 0° C. under Argon was added EDCI (406 mg, 2.12 mmol). Stirring was continued over night and the reaction mixture was allowed to warm up to room temperature. The reaction mixture was poured into aq. 10% KH2PO4 solution followed by extraction with AcOEt (3×). The organic phases were washed once with aq. 10% KH2PO4, aq. sat. NaHCO3 and with aq. sat. NaCl solution. The combined organic phases were dried over Na2SO4, filtered and evaporated to afford the title compound (558 mg, 95%) as light brown solid. MS: 306.2 (M+H+).

後処理

  1. waitwas continued over night
  2. extractionfollowed by extraction with AcOEt (3×)
  3. washThe organic phases were washed once with aq. 10% KH2PO4, aq. sat. NaHCO3 and with aq. sat. NaCl solution
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-14e569cad0f54ce8b3595435e20b96ee
出典データセット
uspto-grants-2015_11
特許番号
US09187429B2

反応ノート

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