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

HRID 1924798

Reaktionsgleichung

Reaktionsgleichung von HRID 1924798
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0d17aa22a9584b3ca9feff3433d9dbd1
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178563B2

Verknüpfte Notizen

Wird geladen…