Pyridine → HCID 22244652, compound

HRID 891127Notes

Reaction equation

HRID 891127 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](O)=[O:11])=[C:5]([CH3:16])[N:4]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH:25][C:26]([NH:28][S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)(=[O:31])=[O:30])=[O:27])=[CH:19][CH:18]=2)[N:3]=1.C(=O)(O)[O-].[NH4+].[N:44]1C=CC=CC=1.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>CN(C)C=O>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([NH2:44])=[O:11])=[C:5]([CH3:16])[N:4]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][NH:25][C:26]([NH:28][S:29]([C:32]3[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=3)(=[O:31])=[O:30])=[O:27])=[CH:21][CH:22]=2)[N:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 22244543HCID 22244543, compound

Product 1

HCID 22244652HCID 22244652, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-[3,5-dimethyl-1-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-1H-pyrazol-4-yl]benzoic acid (step 6, 270 mg, 0.52 mmol) in N,N-dimethylformamide (1 mL) was added ammonium bicarbonate (45 mg, 0.57 mmol), pyridine (0.35 mL) and a solution of di-t-butyldicarbonate (120 mg, 0.57 mmol) in N,N-dimethylformamide (1 mL). The mixture was stirred at room temperature for 1 day. After dilution with water (10 mL), extraction with ethyl acetate (30 mL×3) was followed. The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure. The crude products was purified by TLC with dichloromethane/methanol (10:1) to afford 46 mg (10%) of the title compound as white solids: MS (ESI) m/z 532 [M+H]+, 530 [M−H]−.

Workup

  1. extractionAfter dilution with water (10 mL), extraction with ethyl acetate (30 mL×3)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was removed under reduced pressure
  4. customThe crude products was purified by TLC with dichloromethane/methanol (10:1)

Sources & evidence

ORD record
ord-2c3d09c001774c13959a5160d6f5a11f
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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