Diisopropylethylamine → 4-(2-Amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)-1-(pyrimidin-4-yl)piperidine-4-carboxylic acid dihydrochloride

HRID 412538노트

반응식

HRID 412538 반응식
C([O:3][C:4]([C:6]1([CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][NH:26][CH2:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.C(N(C(C)C)CC)(C)C.[ClH:39].[N:40]1([C:45](N)=[NH:46])C=CC=N1>CN(C)C=O>[ClH:39].[ClH:39].[C:45]([N:26]1[CH2:25][CH2:24][C:23]2[C:28](=[CH:29][C:20]([O:19][CH2:18][C:6]3([C:4]([OH:3])=[O:5])[CH2:7][CH2:8][N:9]([C:12]4[CH:17]=[CH:16][N:15]=[CH:14][N:13]=4)[CH2:10][CH2:11]3)=[CH:21][CH:22]=2)[CH2:27]1)(=[NH:40])[NH2:46]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 600641441-(Pyrimidin-4-yl)-4-(1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidine-4-carboxylic acid ethyl ester

생성물 1

HCID 114090734-(2-Amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)-1-(pyrimidin-4-yl)piperidine-4-carboxylic acid dihydrochloride수율 16.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-(pyrimidin-4-yl)-4-(1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidine-4-carboxylic acid ethyl ester (260 mg) in dimethylformamide (1 ml) were added diisopropylethylamine (0.24 ml) and 1H-pyrazole-1-carboxamidine hydrochloride (200 mg), and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was separated by HPLC (0.05% aqueous trifluoroacetic acid:methanol=6:4-2:8). The obtained residue was refluxed with conc. hydrochloric acid for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was washed with diethyl ether and dried under reduced pressure to give the title compound (51 mg).

후처리

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe obtained residue was separated by HPLC (0.05% aqueous trifluoroacetic acid:methanol=6:4-2:8)
  4. temperatureThe obtained residue was refluxed with conc. hydrochloric acid for 2 hours
  5. customAfter completion of the reaction
  6. customthe solvent was evaporated
  7. washthe obtained residue was washed with diethyl ether
  8. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-d1cb9b52d354405e98bca3581913ea67
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562828B1

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