Triethylamine → 2-((1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl)-2,4-dihydro-4-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)-3H-1,2,4-triazol-3-one

HRID 512815노트

반응식

HRID 512815 반응식
[CH2:1]([O:8][C@H:9]([C@@H:11]([NH:14][NH:15][CH:16]=O)[CH2:12][CH3:13])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[OH:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][N:34]([C:37]3[CH:42]=[CH:41][C:40]([NH:43][C:44](=O)[O:45]C4C=CC=CC=4)=[CH:39][CH:38]=3)[CH2:33][CH2:32]2)=[CH:27][CH:26]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C@H:9]([C@@H:11]([N:14]1[C:44](=[O:45])[N:43]([C:40]2[CH:39]=[CH:38][C:37]([N:34]3[CH2:33][CH2:32][N:31]([C:28]4[CH:29]=[CH:30][C:25]([OH:24])=[CH:26][CH:27]=4)[CH2:36][CH2:35]3)=[CH:42][CH:41]=2)[CH:16]=[N:15]1)[CH2:12][CH3:13])[CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 1317528Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamateHCID 101309112-((1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl)hydrazinecarboxaldehyde

생성물 1

HCID 462232972-((1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl)-2,4-dihydro-4-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)-3H-1,2,4-triazol-3-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
95 °C

실험 절차

A mixture of N′-((2S,3S)-2-(benzyloxy)pentan-3-yl)formohydrazide compound of formula-17 (45.5 g) obtained in example-13, dioxane (500 ml) added phenyl 4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenylcarbamate compound of formula-19 (50 g) was heated to 90-100° C. Triethylamine (26 g) was added to the reaction mixture at 90-100° C. over a period of 1 hour and stirred for 24 hours at 90-100° C. After completion of the reaction, the reaction mixture was cooled to 25-30° C. and dichloromethane was added to the reaction mixture. Filtered the reaction mixture through hyflow bed and washed with dichloromethane. Water was added to the filtrate. Both organic and aqueous layers were separated and the aqueous layer was extracted with dichloromethane. Both organic layers were combined and washed with 2% sodium hydroxide solution followed by water, and then with 5% hydrochloric acid solution followed by water and 5% NaHCO3 solution washing. Distilled off the solvent from organic layer under reduced pressure to get the title compound. Isopropyl alcohol (75 ml) was added to the obtained compound and the reaction mixture was cooled to 25-30° C. The reaction mixture was stirred for 6 hours at 25-30° C. Filtered the solid, washed with isopropyl alcohol and then dried to get the title compound. Yield: 28 g; Purity by HPLC: 97.67%; Impurity-A: 0.37%

후처리

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to 25-30° C.
  3. filtrationFiltered the reaction mixture through hyflow bed
  4. washwashed with dichloromethane
  5. additionWater was added to the filtrate
  6. customBoth organic and aqueous layers were separated
  7. extractionthe aqueous layer was extracted with dichloromethane
  8. washwashed with 2% sodium hydroxide solution
  9. washwashing
  10. distillationDistilled off the solvent from organic layer under reduced pressure

출처 및 근거

ORD 기록
ord-8ff31652cdd24327a0de78b9870aa38b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102664B2

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