Triethylamine → HCID 178520558、化合物

HRID 1480459ノート

反応式

HRID 1480459 の反応式
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=2)=[O:8])[CH2:3]1.[NH:19]1[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][C:27](O)=[O:28])[N:21]=[N:20]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C)C=O>[NH:19]1[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][C:27]([NH:1][CH:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=3)=[O:8])[CH2:3]2)=[O:28])[N:21]=[N:20]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86722684HCID 86722684、化合物HCID 178525383HCID 178525383、化合物2 回

生成物 1

HCID 178520558HCID 178520558、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture comprising of 3,5-dichlorobenzyl 3-aminopyrrolidine-1-carboxylate (1 equiv), 4-(1H-1,2,3-triazol-4-yl)butanoic acid (1 equiv.), HATU (1.5 equiv.) and triethylamine (5 equiv.) in dimethylformamide was stirred at RT for 18 hours. Another 1 equivalent of 4-(1H-1,2,3-triazol-4-yl)butanoic acid was added to the reaction mixture and stirring continued for a further 2 hours. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with DCM. The organic portion was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was dry loaded using silica onto a 12 g ISCO column, eluting with 0-15% MeOH in DCM. The product fractions were combined and concentrated under reduced pressure. Further purification was carried our using preparative LC-MS. The product fractions were concentrated under reduced pressure to give an aqueous solution and extracted with EtOAc to afford the title compound;

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. customThe organic portion was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dry with materialThe crude product was dry
  9. washeluting with 0-15% MeOH in DCM
  10. concentrationconcentrated under reduced pressure
  11. customFurther purification
  12. concentrationThe product fractions were concentrated under reduced pressure
  13. customto give an aqueous solution
  14. extractionextracted with EtOAc

出典と根拠

ORDレコード
ord-b118fac3c7e34e2282ffb9d7096436da
出典データセット
uspto-grants-2016_08
特許番号
US09409895B2

反応ノート

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