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Acetic Acid → 4-Hydroxy-6-oxo-3-{2'-[({2-[4-(trifluoromethyl)phenyl]ethyl}amino)methyl]-1,1'-biphenyl-4-yl}-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

HRID 1244096
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HRID 1244096 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([OH:24])=[C:21]([C:25]#[N:26])[C:20](=[O:27])[NH:19][C:18]=3[S:17][CH:16]=2)=[CH:11][CH:10]=1)=O.C(O)(=O)C.[F:32][C:33]([F:44])([F:43])[C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][NH2:42])=[CH:36][CH:35]=1.C([BH3-])#N>CO.ClCCl>[OH:24][C:22]1[C:23]2[C:15]([C:12]3[CH:13]=[CH:14][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[CH2:1][NH:42][CH2:41][CH2:40][C:37]4[CH:36]=[CH:35][C:34]([C:33]([F:32])([F:43])[F:44])=[CH:39][CH:38]=4)=[CH:10][CH:11]=3)=[CH:16][S:17][C:18]=2[NH:19][C:20](=[O:27])[C:21]=1[C:25]#[N:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 19881062-[4-(Trifluoromethyl)phenyl]ethan-1-amineHCID 546899423-(2'-Formyl-1,1'-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

생성물 1

HCID 546780564-Hydroxy-6-oxo-3-{2'-[({2-[4-(trifluoromethyl)phenyl]ethyl}amino)methyl]-1,1'-biphenyl-4-yl}-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-(2′-formyl-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.025 g, 0.067 mmol) in MeOH (1 mL) and dichloromethane (1 mL, with 2% v/v acetic acid) was added 2-(4-trifluoromethyl phenyl)ethyl amine (0.025 g, 0.13 mmol) and shaken at room temperature for 10 min. MP-cyanoborohydride (0.09 g, 0.2 mmol) was then added to the reaction mixture and shaken at room temperature for 24 h. The reaction was filtered, concentrated and purified by RP-HPLC to give the title compound. MS (ESI) m/e 546 (M+H)+; 1H NMR (500 MHz, DMSO-d6): δ ppm 11.11 (br s, 1H), 8.97 (br s, 2H), 7.66–7.70 (m, 3H), 7.58 (d, 2H), 7.50–7.54 (m, 2H), 7.46 (d, 2H), 7.37–7.40 (m, 1H), 7.30 (d, 2H), 6.76 (s, 1H), 4.24 (s, 2H), 3.17 (br s, 2H), 2.95 (t, 2H).

후처리

  1. stirringshaken at room temperature for 24 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. custompurified by RP-HPLC

출처 및 근거

ORD 기록
ord-a59af4cc29ae435eb4e6b114765ccd74
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07119205B2

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