Hydrochloric Acid → N-(2-hydroxyethyl)-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide hydrochloride

HRID 1622177노트

반응식

HRID 1622177 반응식
C(C1C=CC(N2CC[C@H](N[C@@H](C3C4C(=CC=CC=4)C=CC=3)C)C2)=CC=1)(=O)C.[OH:28][CH2:29][CH2:30][NH:31][C:32](=[O:57])[C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:43][CH2:42][C@H:41]([NH:44][C@@H:45]([C:47]3[C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[CH:50]=[CH:49][CH:48]=3)[CH3:46])[CH2:40]2)=[CH:35][CH:34]=1.[ClH:58]>C(Cl)Cl.O1CCOCC1>[ClH:58].[OH:28][CH2:29][CH2:30][NH:31][C:32](=[O:57])[C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:43][CH2:42][C@H:41]([NH:44][C@@H:45]([C:47]3[C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[CH:50]=[CH:49][CH:48]=3)[CH3:46])[CH2:40]2)=[CH:35][CH:34]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 58973483(S)-1-(4-acetylphenyl)pyrrolidin-3-yl-[(R)-1-(naphthalen-1-yl)ethyl]amineHCID 58973499N-(2-hydroxyethyl)-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide

생성물 1

HCID 67407335N-(2-hydroxyethyl)-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide hydrochloride

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a mixed solution of 7.7 mg of 2-aminoethanol and 50 mg of 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzoic acid hydrochloride (the compound obtained in Example 3.001) dissolved in 8 ml of dimethylformamide were added 22.2 mg of 1-hydroxybenzotriazole, 70 μl of triethylamine and 31.4 mg of EDC hydrochloride, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was evaporated, a saturated aqueous sodium bicarbonate solution and chloroform were added to the residue, and the mixture was stirred and the liquids were separated. The organic layer was dried and concentrated, and the residue was purified by NH thin layer silica gel chromatography (chloroform:methanol=39:1) and thin layer silica gel chromatography (chloroform:methanol=9:1) to give 22.6 mg of N-(2-hydroxyethyl)-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide. (2) To a solution of 22.6 mg of N-(2-hydroxyethyl)-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide dissolved in 1 ml of methylene chloride was added dropwise 3 ml of a solution of 4M hydrochloric acid in dioxane, and the mixture was stirred for a while. The reaction mixture was evaporated, and, to the residue was added tert-butanol to dissolve the same, and freeze-dried to obtain 25.6 mg of N-(2-hydroxyethyl)-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide hydrochloride (the following Table A3, Example 3.017).

후처리

  1. customThe reaction mixture was evaporated
  2. additionto the residue was added tert-butanol
  3. dissolutionto dissolve the same, and
  4. customfreeze-dried

출처 및 근거

ORD 기록
ord-69f67e270d6c4c48ae329de7e94e1f03
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778628B2

반응 노트

불러오는 중…