Triethylamine → 4'-Cyano-6-methyl-biphenyl-3-carboxylic acid [4-(morpholine-4-sulfonyl)-phenyl]-amide

HRID 1890249

反応式

HRID 1890249 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]([OH:18])=O)[CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(Cl)(=O)C(Cl)=O.[N:25]1([S:31]([C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[N:25]1([S:31]([C:34]2[CH:35]=[CH:36][C:37]([NH:40][C:16]([C:11]3[CH:10]=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=4)[C:14]([CH3:15])=[CH:13][CH:12]=3)=[O:18])=[CH:38][CH:39]=2)(=[O:33])=[O:32])[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2107944-(Morpholinosulfonyl)anilineHCID 594367094'-Cyano-6-methyl-biphenyl-3-carboxylic acid

生成物 1

HCID 251244404'-Cyano-6-methyl-biphenyl-3-carboxylic acid [4-(morpholine-4-sulfonyl)-phenyl]-amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 4′-cyano-6-methyl-biphenyl-3-carboxylic acid 3 (40 mg, 0.17 mmol) in anhydrous methylene chloride (5 ml) is added 2 drops of DMF. Then oxalyl chloride (32 mg, 22 μl, 0.25 mmol) is added. The mixture is stirred at ambient temperature until it turns clear. After that, it is concentrated, re-dissolved in anhydrous methylene chloride (3 ml), and added to a solution of 4-(morpholine-4-sulfonyl)-phenylamine (61 mg, 0.25 mmol) and triethylamine (34 mg, 47 μl, 0.33 mmol) in methylene chloride (2 ml). The mixture is stirred for 2 hours, concentrated and the residue is purified by preparative mass triggered HPLC (C18 column, eluted with CH3CN—H2O containing 0.05% TFA) to give 4′-cyano-6-methyl-biphenyl-3-carboxylic acid [4-(morpholine-4-sulfonyl)-phenyl]-amide: 1H NMR (DMSO-d6) δ 10.64 (s, 1H), 8.07 (d, 2H, J=8.8 Hz), 7.97 (d, 2H, J=8.4 Hz), 7.95 (d, 1H, J=8.8 Hz), 7.89 (s, 1H), 7.43 (d, 2H, J=8.4 Hz), 7.67 (d, 2H, J=8.8 Hz), 7.53 (d, 2H, J=8.8 Hz), 3.63 (m, 4H), 2.84 (m, 4H) 2.32 (s, 3H); LC-MS m/z: 462.1 (M+1).

後処理

  1. concentrationAfter that, it is concentrated
  2. dissolutionre-dissolved in anhydrous methylene chloride (3 ml)
  3. stirringThe mixture is stirred for 2 hours
  4. concentrationconcentrated
  5. customthe residue is purified by preparative mass
  6. washHPLC (C18 column, eluted with CH3CN—H2O containing 0.05% TFA)

出典と根拠

ORDレコード
ord-0b1f8fc9f96c4cd79e5044595148534d
出典データセット
uspto-grants-2013_08
特許番号
US08507471B2

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