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Triethylamine → n-(4-{[(1h-Benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide

HRID 970913
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HRID 970913 반응식
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=O.[NH2:12][CH2:13][C:14]1[CH:41]=[CH:40][C:17]([CH2:18][N:19]([CH2:30][C:31]2[NH:35][C:34]3[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=3[N:32]=2)[CH:20]2[C:29]3[N:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.CCN(CC)CC>O=S(Cl)Cl.CN(C1C=CN=CC=1)C>[NH:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=[C:31]1[CH2:30][N:19]([CH2:18][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][NH:12][C:4](=[O:6])[C:3]2[C:7]([CH3:11])=[CH:8][CH:9]=[N:10][C:2]=2[CH3:1])=[CH:41][CH:40]=1)[CH:20]1[C:29]2[N:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:23][CH2:22][CH2:21]1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 15125612,4-Dimethyl-3-pyridinecarboxylic acidHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

생성물 1

HCID 20747324n-(4-{[(1h-Benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2,4-dimethyl-nicotinamide수율 33%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 24386Thionyl Chloride용매

실험 절차

A solution of 2,4-dimethyl-nicotinic acid (54 mg, 0.35 mmol) in SOCl2 (˜2 mL, excess) was heated to 80° C. for 4 hours. The condenser was removed and the mixture was flushed with N2 at 80° C. for ˜5 minutes and then dried in vacuo for 10 minutes. The resulting syrup was dissolved in CH2Cl2 (2.4 mL) and added to a stirring mixture of (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (187 mg, 0.47 mmol), Et3N (0.33 mL, 2.35 mmol) and a catalytic amount of DMAP. The reaction mixture was stirred overnight at room temperature. Purification of the crude yellow foam (240 mg) by radial chromatography on silica gel (2 mm plate, CH2Cl2/MeOH/NH4OH, 100:2:1) followed by radial chromatography on silica gel (1 mm plate, EtOAc/MeOH/NH4OH, 400:3:3) afforded the desired amide (61 mg, 33%) as a white foam.

후처리

  1. customThe condenser was removed
  2. customthe mixture was flushed with N2 at 80° C. for ˜5 minutes
  3. customdried in vacuo for 10 minutes
  4. dissolutionThe resulting syrup was dissolved in CH2Cl2 (2.4 mL)
  5. customPurification of the crude yellow foam (240 mg) by radial chromatography on silica gel (2 mm plate, CH2Cl2/MeOH/NH4OH, 100:2:1)

출처 및 근거

ORD 기록
ord-2f3589c1e9984ebb8b68f67bccaff70b
출처 데이터셋
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07312234B2

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