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

HRID 1924798

반응식

HRID 1924798 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

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 t, 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 (C1-8 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, 1 H), 8.07 (d, 2 H, J=8.8 Hz), 7.97 (d, 2 H, J=8.4 Hz), 7.95 (d, 1 H, J=8.8 Hz), 7.89 (s, 1 H), 7.43 (d, 2 H, J=8.4 Hz), 7.67 (d, 2 H, J=8.8 Hz), 7.53 (d, 2 H, J=8.8 Hz), 3.63 (m, 4 H), 2.84 (m, 4 H) 2.32 (s, 3 H); LC-MS m/z: 462.1 (M+1).

후처리

  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 (C1-8 column, eluted with CH3CN—H2O containing 0.05% TFA)

출처 및 근거

ORD 기록
ord-0d17aa22a9584b3ca9feff3433d9dbd1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178563B2

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