(2S)-Pyrrolidine-2-carbonitrile hydrochloride → (S)-1-[(2S,4R)-4-(5-cyano-2-pyridyl)amino-2-pyrrolidinylcarbonyl]-2-cyanopyrrolidine dihydrochloride

HRID 1791893노트

반응식

HRID 1791893 반응식
C(OC([N:8]1[CH2:12][C@H:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][N:15]=2)[CH2:10][C@H:9]1[C:22]([OH:24])=O)=O)(C)(C)C.[ClH:25].[C:26]([C@@H:28]1[CH2:32][CH2:31][CH2:30][NH:29]1)#[N:27]>CN(C=O)C>[ClH:25].[ClH:25].[C:20]([C:17]1[CH:18]=[CH:19][C:14]([NH:13][C@H:11]2[CH2:12][NH:8][C@H:9]([C:22]([N:29]3[CH2:30][CH2:31][CH2:32][C@H:28]3[C:26]#[N:27])=[O:24])[CH2:10]2)=[N:15][CH:16]=1)#[N:21]

참가 물질

4

반응물 2

HCID 44593801(2S)-Pyrrolidine-2-carbonitrile hydrochlorideHCID 67506632(2S,4R)-1-tert-Butoxycarbonyl-4-(5-cyano-2-pyridyl)aminopyrrolidine-2-carboxylic acid

생성물 1

HCID 67507587(S)-1-[(2S,4R)-4-(5-cyano-2-pyridyl)amino-2-pyrrolidinylcarbonyl]-2-cyanopyrrolidine dihydrochloride

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(2S,4R)-1-tert-Butoxycarbonyl-4-(5-cyano-2-pyridyl)aminopyrrolidine-2-carboxylic acid (title compound of Reference Example 4, 0.73 g) and (S)-2-cyanopyrrolidine hydrochloride (0.29 g) were dissolved in DMF (10 mL), and triethylamine (0.62 mL), HOBT (0.34 g) and EDC hydrochloride (0.42 g) were successively added thereto. The mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried and evaporated under reduced pressure. The residue was purified by silica gel chromatography to give (S)-1-[(2S,4S)-1-tert-butoxycarbonyl-4-(5-cyano-2-pyridyl) amino-2-pyrrolidinylcarbonyl]-2-cyanopyrrolidine (0.58 g) as amorphous.

출처 및 근거

ORD 기록
ord-f4aa30a3e9374e00a8e16b40d26689e9
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074794B2

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