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 1011886노트

반응식

HRID 1011886 반응식
[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

참가 물질

6

반응물 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 acid2회

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-60f6cb077d0f416fb0f5d82177afa491
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977358B2

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