Hydrochloric Acid → 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride

HRID 1183022노트

반응식

HRID 1183022 반응식
C(OC(=O)[NH:7][C@H:8]([CH2:12][NH:13][C:14]([C:16]1[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=1)=[O:15])[CH2:9][CH2:10][CH3:11])(C)(C)C.Cl>O1CCOCC1>[ClH:24].[NH2:7][C@@H:8]([CH2:9][CH2:10][CH3:11])[CH2:12][NH:13][C:14]([C:16]1[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=1)=[O:15]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86651887((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester

생성물 1

HCID 866518883,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To a solution of ((S)-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester (1.30 g, 3.49 mmol) in 1,4-dioxane (20 mL) is added HCl (50 mL of a 4 M solution in 1,4-dioxane, 200 mmol) and the reaction mixture is stirred at RT for 16 h. The reaction mixture is concentrated in vacuo and the yellow solid obtained is triturated with diethyl ether; the diethyl ether layer is decanted and the product is dissolved in a minimal volume of MeOH and is precipitated by the addition of diethyl ether. The solvent is decanted and the resulting solid is dried under vacuum to afford the title compound. [M+H]+ 233. 1H NMR (400 MHz, CDCl3) δ 8.16 (1H, t), 7.89 (2H, br), 7.07 (4H, br), 3.42-3.38 (2H, m), 3.27-3.18 (1H, m), 1.54-1.47 (2H, m), 1.44-1.35 (2H, m), 0.89 (3H, t).

후처리

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe yellow solid obtained
  3. customis triturated with diethyl ether
  4. customthe diethyl ether layer is decanted
  5. dissolutionthe product is dissolved in a minimal volume of MeOH
  6. customis precipitated by the addition of diethyl ether
  7. customThe solvent is decanted
  8. customthe resulting solid is dried under vacuum

출처 및 근거

ORD 기록
ord-3aa6ae72904c4631b107490ae524f89d
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664228B2

반응 노트

불러오는 중…