Diisopropylethylamine → 2-(3-Pyridyl)-pyrimidine-5-carboxylic-acid-3-methylsulfamoyl-benzylamide

HRID 219688Notes

Reaction equation

HRID 219688 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][N:9]=2)[CH:3]=1.C(N(C(C)C)CC)(C)C.Cl.[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:14]([C:11]1[CH:12]=[N:13][C:8]([C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)=[N:9][CH:10]=1)=[O:16])(=[O:30])=[O:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 691225733-Methylsulfamoylbenzylamine hydrochlorideHCID 691231392-(3-Pyridyl)-pyrimidine-5-carboxylic acid hydrochloride

Product 1

HCID 598058382-(3-Pyridyl)-pyrimidine-5-carboxylic-acid-3-methylsulfamoyl-benzylamideYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(3-pyridyl)-pyrimidine-5-carboxylic acid hydrochloride (237 mg 1 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (380 mg, 1 mmol) in dry DMF (15 mL) is treated with diisopropylethylamine (0.36 mL) and stirred at room temperature for 30 min. 3-Methylsulfamoylbenzylamine hydrochloride (355 mg, 1.5 mmol) is added and the mixture is stirred at room temperature for 24 hours. The solvent is removed and the residue is partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase is separated, washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is triturated with EtOAc. The resulting solid is filtered, washed with ether to afford 2-(3-pyridyl)-pyrimidine-5-carboxylic-acid-3-methylsulfamoyl-benzylamide (185 mg, 48%). MS: 384 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 2.43 (d, 3H), 4.65 (d, 2H), 7.45-7.55 (q, 1H), 7.60-7.75 (m, 3H), 7.80 (s, 1H), 8.72-8.80 (m, 2H), 9.35 (s, 2H), 9.55 (m, 2H).

Workup

  1. stirringthe mixture is stirred at room temperature for 24 hours
  2. customThe solvent is removed
  3. customthe residue is partitioned between EtOAc and saturated aqueous NaHCO3
  4. customThe organic phase is separated
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is triturated with EtOAc
  10. filtrationThe resulting solid is filtered
  11. washwashed with ether

Sources & evidence

ORD record
ord-488abf869e0d4d98aa2ba31c8b9cb82f
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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