Triethylamine → HCID 131730942, compound

HRID 2035490Notes

Reaction equation

HRID 2035490 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:23][C:24]([NH2:26])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([S:30](Cl)(=[O:32])=[O:31])[CH2:28][CH3:29].C(N(CC)CC)C.O.N>ClCCl>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][S:30]([CH2:27][CH2:28][CH3:29])(=[O:32])=[O:31])=[CH:20][CH:21]=2)[N:12]=[CH:11][C:10]=1[CH2:23][C:24]([NH2:26])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 12896473Azane;hydrateHCID 131730943HCID 131730943, compound

Product 1

HCID 131730942HCID 131730942, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

39 mg of 4-(benzylamino)-6-{(4-aminophenyl)amino) pyridine-3-carboxyamide (the compound of Example 65), 83 mg of 1-propanesulfonyl chloride and 67 mg of triethylamine in 1.5 mL of dichloromethane were stirred at room temperature for 1 hour. Under ice cooling, ammonia water was added to the reaction mixture, and stirred for 5 minutes. The reaction mixture was extracted with chloroform, and the extract was dried on anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (chloroform:ammonia methanol=10:1) to obtain 12 mg (19%) of the title compound as a light brown crystalline powder.

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. dry with materialthe extract was dried on anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (chloroform:ammonia methanol=10:1)

Sources & evidence

ORD record
ord-048701f9cd0a4f088b2adabb0368e2fb
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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