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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
ノート
印刷プレビュー

反応式

HRID 1244096 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-a59af4cc29ae435eb4e6b114765ccd74
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07119205B2

反応ノート

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