Triethylamine → HCID 12001815, compound

HRID 656465Notes

Reaction equation

HRID 656465 reaction equation
[O:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=[CH:2]1.[NH:9]1[CH2:13][CH2:12][C:11]2([N:18]3[CH:19]=[N:20][CH:21]=[C:17]3[CH2:16][CH2:15][CH2:14]2)[CH2:10]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[O:1]1[C:5]([C:6]([N:9]2[CH2:13][CH2:12][C:11]3([N:18]4[CH:19]=[N:20][CH:21]=[C:17]4[CH2:16][CH2:15][CH2:14]3)[CH2:10]2)=[O:8])=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 16340557Oxazole-5-carboxylic AcidHCID 68575306HCID 68575306, compound

Product 1

HCID 12001815HCID 12001815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.5 mmol of oxazole-5-carboxylic acid [118994-90-4] are dissolved in 5 ml of dichloro-methane and the solution is admixed at 0° C. with 1.6 mmol of chlorenamine. The reaction solution is subsequently stirred at room temperature for an hour and then added dropwise at 0° C. to a solution of 1 mmol of 7,8-dihydro-6H-spiro[imidazo[1,5-a]pyridine-5,3′-pyrrolidine] (Example 3a) and 2 mmol of triethylamine in 5 ml of dichloromethane. The reaction mixture is subsequently stirred at room temperature for 3 hours, poured into saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (3×). The combined organic extracts are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60 F) on the basis of the Rf value.

Workup

  1. customis admixed at 0° C. with 1.6 mmol of chlorenamine
  2. stirringThe reaction mixture is subsequently stirred at room temperature for 3 hours
  3. extractionextracted with dichloromethane (3×)
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried with sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-3410cf97abe74e1682f331873a2a010f
Source dataset
uspto-grants-2011_12
Patent number
US08071773B2

Reaction notes

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