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Diisopropylethylamine → 2-(2,5-Difluoro-phenyl)-pyrimidine-5-carboxylic acid 3-methylsulfamoyl-benzylamide

HRID 219654
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 219654
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][N:10]=1.C(N(C(C)C)CC)(C)C.[CH3:27][NH:28][S:29]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH2:36])(=[O:31])=[O:30]>CN(C=O)C>[CH3:27][NH:28][S:29]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH:36][C:15]([C:12]1[CH:13]=[N:14][C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])=[N:10][CH:11]=1)=[O:17])(=[O:30])=[O:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 167855973-(aminomethyl)-N-methylbenzenesulfonamideHCID 450733642-(2,5-Difluorophenyl)pyrimidine-5-carboxylic acid

Produkt 1

HCID 598058362-(2,5-Difluoro-phenyl)-pyrimidine-5-carboxylic acid 3-methylsulfamoyl-benzylamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

A mixture of 2-(2,5-difluoro-phenyl)-pyrimidine-5-carboxylic acid (118 mg, 0.5 mmol, prepared according to the general procedure described in Example 2, steps 1 and 2), and 0-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (190 mg, 0.5 mmol) in dry DMF (5 mL) is treated with 0.09 mL of diisopropylethylamine and stirred at room temperature for 30 minutes. A solution of 3-methylsulfamoylbenzylamine (150 mg, 0.75 mmol) in dry DMF (1 mL) is added and the mixture stirred at room temperature for 24 hours. The solvent is removed and the residue partitioned between EtOAc and saturated NaHCO3. The organic phase is separated and washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by column chromatography eluting with 20% EtOAc in DCM to afford 2-(2,5-difluoro-phenyl)-pyrimidine-5-carboxylic acid 3-methylsulfamoyl-benzylamide (135 mg, 65%) as a solid. MS: 419 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 2.41 (d, 3H), 4.64 (d, 2H), 7.43-7.78 (m, 5H), 7.89 (s, 1H) 7.90 (t, 1H), 9.37 (s, 2H), 9.60 (t, 1H).

Aufarbeitung

  1. customprepared
  2. stirringthe mixture stirred at room temperature for 24 hours
  3. customThe solvent is removed
  4. customthe residue partitioned between EtOAc and saturated NaHCO3
  5. customThe organic phase is separated
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by column chromatography
  11. washeluting with 20% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-e6d68e02de0a46b59b058c36ae0745a9
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08202863B2

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