Triethylamine → (1-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazol-4-yl)-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanone

HRID 1011886

反応式

HRID 1011886 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]([N:16]3[C:20]([CH2:21][CH3:22])=[C:19]([C:23](O)=[O:24])[C:18]([CH2:26][CH3:27])=[N:17]3)[CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[N:59]1([CH2:66][CH2:67][OH:68])[CH2:65][CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]([N:16]3[C:20]([CH2:21][CH3:22])=[C:19]([C:23]([N:62]4[CH2:63][CH2:64][CH2:65][N:59]([CH2:66][CH2:67][OH:68])[CH2:60][CH2:61]4)=[O:24])[C:18]([CH2:26][CH3:27])=[N:17]3)[CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 27365502-(1,4-Diazepan-1-yl)ethan-1-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673139751-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid2 回

生成物 1

HCID 57555028(1-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazol-4-yl)-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 0.20 g (0.50 mmol) of 1-{3-[(E)-2-(4-chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid (intermediate 1) and 0.21 g (0.50 mmol) of HATU were dissolved in 8 ml of DMF at RT. While stirring, 0.16 g=0.22 ml (1.60 mmol) of Et3N were added drop by drop. After 30 min, a solution of 0.076 g (0.50 mmol) of 2-[1,4]diazepan-1-yl-ethanol in 2 ml of DMF were added drop by drop and stirring was continued for 20 hours at RT. The reaction mixture was poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0-9:1) to afford the title compound as colorless oil. MS: 507.4 (MH+, 1 Cl).

後処理

  1. stirringstirring
  2. waitwas continued for 20 hours at RT
  3. additionThe reaction mixture was poured
  4. extractionextracted twice with EtOAc
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0-9:1)

出典と根拠

ORDレコード
ord-60f6cb077d0f416fb0f5d82177afa491
出典データセット
uspto-grants-2011_07
特許番号
US07977358B2

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