N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine → HCID 69296208, 화합물

HRID 1624340노트

반응식

HRID 1624340 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:15]1[C:24]2[N:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:18][CH2:17][CH2:16]1)[CH2:12][CH2:13][NH2:14].[C:25]([O:29][C:30]([NH:32][C:33](N1C=CC=N1)=[N:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:31])([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[C:38]([O:37][C:35]([NH:34][C:33]([NH:32][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])=[N:14][CH2:13][CH2:12][N:11]([CH2:10][C:2]1[NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=1)[CH:15]1[C:24]2[N:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:18][CH2:17][CH2:16]1)=[O:36])([CH3:41])([CH3:40])[CH3:39]

참가 물질

4

반응물 2

HCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 10149770N-(1H-benzimidazol-2-ylmethyl)-N-(5,6,7,8-tetrahydroquinolin-8-yl)-ethane-1,2-diamine

생성물 1

HCID 69296208HCID 69296208, 화합물수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Using General Procedure B: Reaction of N-(tert-butoxycarbonyl)-2-amino-acetaldehyde (0.204 g, 1.28 mmol) and (1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.284 g, 1.02 mmol) with NaBH(OAc)3 (0.430 g, 2.03 mmol) in CH2Cl2 (10 mL) provided 0.71 g of a yellow foam. The foam was dissolved in THF (10 mL) and treated with 6N hydrochloric acid (10 mL). The resultant solution was stirred at room temperature overnight. The solution was neutralized with solid K2CO3 (5 g), diluted with water (5 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH) provided 0.205 g (64%) of N1-(1H-Benzimidazol-2-ylmethyl)-1-(5,6,7,8-tetrahydro-quinolin-8-yl)-ethane-1,2-diamine as a yellow solid. To a solution of N1-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-ethane-1,2-diamine (0.205 g, 0.64 mmol) in dry THF (6 mL) was added N.N′-bis-(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (Tetrahedron Lett. 1993, 34, 3389.) (0.201 g, 0.64 mmol) and the resultant mixture was stirred at room temperature for 18 hours. The mixture was concentrated and the resultant oil was purified by column chromatography on silica gel (40:1:1 CH2Cl2—CH3OH—NH4OH) and provided 0.267 g (74%) of N,N′-bis(tert-butoxycarbonyl)-N″-{2-[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-ethyl}-guanidine as a white foam.

후처리

  1. concentrationThe mixture was concentrated
  2. customthe resultant oil was purified by column chromatography on silica gel (40:1:1 CH2Cl2—CH3OH—NH4OH)

출처 및 근거

ORD 기록
ord-94af3cbd7af24319a8320117c6c7f704
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778967B2

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