Acetic Acid → Bavisant

HRID 13557

반응식

HRID 13557 반응식
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O[C:25]1(O[Si](C)(C)C)[CH2:27][CH2:26]1)C.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH:25]1([N:19]2[CH2:18][CH2:17][N:16]([C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[CH:13][CH:12]=3)=[O:15])[CH2:21][CH2:20]2)[CH2:27][CH2:26]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 59218186(4-Morpholin-4-ylmethyl-phenyl)piperazin-1-yl-methanone

생성물 1

HCID 16061509Bavisant

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

A solution of (4-morpholin-4-ylmethyl-phenyl)-piperazin-1-yl-methanone (0.128 g) in methanol (7.5 mL) was treated with (1-ethoxy-cyclopropoxy)-trimethyl-silane (1.5 mL), acetic acid (0.2 mL), and NaBH3CN (˜400 mg). The mixture was heated at 60° C. for 18 h, and then was cooled to room temperature and concentrated. The residue was diluted with 1 N NaOH and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (SiO2) to yield the title compound.

후처리

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated
  3. additionThe residue was diluted with 1 N NaOH
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (SiO2)

출처 및 근거

ORD 기록
ord-7ed386d7e56a467c9382415fc0799b9b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728129B2

연결된 노트

불러오는 중…