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Triethylamine → 4-[1,2,4]Triazol-1-yl-benzoic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide

HRID 2367741
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HRID 2367741 반응식
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.Cl.Cl.[NH2:17][CH2:18][C:19]1[CH:20]=[C:21]([CH:36]=[CH:37][CH:38]=1)[C:22]([NH:24][C:25]1[CH:34]=[C:33]2[C:28]([CH2:29][CH2:30][N:31]([CH3:35])[CH2:32]2)=[CH:27][CH:26]=1)=[O:23].C(N(CC)CC)C>CN(C=O)C.O.FC(F)(F)C(O)=O>[CH3:35][N:31]1[CH2:30][CH2:29][C:28]2[C:33](=[CH:34][C:25]([NH:24][C:22]([C:21]3[CH:20]=[C:19]([CH:38]=[CH:37][CH:36]=3)[CH2:18][NH:17][C:10](=[O:12])[C:9]3[CH:8]=[CH:7][C:6]([N:1]4[CH:5]=[N:4][CH:3]=[N:2]4)=[CH:14][CH:13]=3)=[O:23])=[CH:26][CH:27]=2)[CH2:32]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 7365314-(1H-1,2,4-Triazol-1-yl)benzoic acidHCID 666490723-(2-Methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)benzylamine dihydrochloride

생성물 1

HCID 666561554-[1,2,4]Triazol-1-yl-benzoic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide수율 61.4%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 6422Trifluoroacetic acid용매

실험 절차

Dissolve 4-[1,2,4]triazol-1-yl-benzoic acid (29 mg, 0.15 mmol) and CDI (N,N′-carbonyldiimidazole) (25 mg, 0.15 mmol) in DMF (2 mL) and stir the mixture for 1 h. To this add 3-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide dihydrochloride (50 mg, 0.14 mmol) and triethylamine (0.095 mL, 0.68 mmol) and stir the mixture overnight. Dilute the mixture with water (1 mL) and trifluoroacetic acid (0.2 mL) and purify by prep-HPLC (5%-70%, CH3CN/H2O) to give the desired product 4-[1,2,4]triazol-1-yl-benzoic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide (51 mg, 0.086 mmol). MS, electrospray 467.4 (M+H), rt 1.05 min.

후처리

  1. custompurify by prep-HPLC (5%-70%, CH3CN/H2O)

출처 및 근거

ORD 기록
ord-b55b6da6675d4c178bf3050d6b670a22
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08697911B2

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