Hydrochloride methanol → (2E)-3-(6-{[(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)-N-hydroxyacrylamide dihydrochloride

HRID 226484노트

반응식

HRID 226484 반응식
[CH:1]1([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([N:12]([C:20]3[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28](=[O:37])[NH:29][O:30]C4CCCCO4)=[CH:22][N:21]=3)C(=O)OC(C)(C)C)[CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[ClH:40]>CO>[ClH:40].[ClH:40].[CH:1]1([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][C:20]3[N:21]=[CH:22][C:23](/[CH:26]=[CH:27]/[C:28]([NH:29][OH:30])=[O:37])=[CH:24][CH:25]=3)[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 2

HCID 21893726Hydrochloride methanolHCID 86603680tert-butyl [(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl](5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl)-2-pyridinyl)carbamate

생성물 1

HCID 86603812(2E)-3-(6-{[(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)-N-hydroxyacrylamide dihydrochloride수율 85%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of tert-butyl [(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl](5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl}-2-pyridinyl)carbamate (179 mg, 0.35 mmol) in MeOH (1 mL) was added hydrogen chloride methanol reagent 10 (3 mL, Tokyo Kasei), and the mixture was stirred at ambient temperature for 1 hr. The solvent was removed in vacuo and the residue was dissolved in dioxane (1 mL). To the reaction mixture was added 4N HCl in dioxane (4 mL) and stirred for 1 hr at ambient temperature. To the reaction mixture was added MeCN and the solvent was removed in vacuo. Obtained colorless solid was triturated with MeCN to give (2E)-3-(6-{[(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)-N-hydroxyacrylamide dihydrochloride (115 mg, 85%) as colorless powder.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dioxane (1 mL)
  3. additionTo the reaction mixture was added 4N HCl in dioxane (4 mL)
  4. stirringstirred for 1 hr at ambient temperature
  5. additionTo the reaction mixture was added MeCN
  6. customthe solvent was removed in vacuo
  7. customObtained colorless solid
  8. customwas triturated with MeCN

출처 및 근거

ORD 기록
ord-be6668cc2c4c4abf9acdc7cf504a86ac
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557127B2

반응 노트

불러오는 중…