Triethylamine → HCID 12094934, compound

HRID 396446Notes

Reaction equation

HRID 396446 reaction equation
[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH2:18][C:19](O)=[O:20])=[CH:15][CH:14]=[C:13]([Cl:22])[CH:12]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:24][NH:25][CH3:26].C(N(CC)CC)C.P(C#N)(=O)(OCC)OCC>CN(C=O)C.O>[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH2:18][C:19]([N:25]([CH3:26])[CH3:24])=[O:20])=[CH:15][CH:14]=[C:13]([Cl:22])[CH:12]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 76257Diethyl cyanophosphonateHCID 9819110HCID 9819110, compound

Product 1

HCID 12094934HCID 12094934, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-benzoyl-6-chloro-1H-indol-3-yl)acetic acid (Example 2, 140 mg, 0.45 mmol), dimethylamine hydrochloride (45 mg, 0.54 mmol) and triethylamine (0.1 ml, 0.54 mmol) in DMF (2 ml) at 0° C. was added diethyl phosphorocyanidate (DEPC, 0.1 ml, 0.54 mmol). The mixture was then stirred at room temperature for 1 h. The mixture was poured into water (20 ml) and extracted with diethyl ether (50 ml×2). The organic extracts were washed with water (30 ml×2), dried (MgSO4) and concentraied. The residual solids were recrystallized from ethyl acetate/hexane to afford 50 mg (33%) of the title compound.

Workup

  1. extractionextracted with diethyl ether (50 ml×2)
  2. washThe organic extracts were washed with water (30 ml×2)
  3. dry with materialdried (MgSO4)
  4. customThe residual solids were recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-88b4d4d546ca4e8085c02fd57d1d3037
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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