Triethylamine → HCID 22167069, compound

HRID 1031950Notes

Reaction equation

HRID 1031950 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[C:7]1([N:13]2[CH2:17][CH2:16][C:15]([NH:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>O1CCCC1>[C:7]1([N:13]2[CH2:17][CH2:16][C:15]([N:18]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[C:4](=[O:5])[O:3][CH2:1][CH3:2])=[N:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178420453HCID 178420453, compound

Product 1

HCID 22167069HCID 22167069, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylchloroformate (0.75 ml) was added dropwise to a solution of 4,5-dihydro-1-phenyl-N-(3-pyridinyl)-1H-pyrazol-3-amine (1.66 g) and triethylamine (2.85 ml) in tetrahydrofuran (150 ml) at -45° under N2. The solution was allowed to warm to room temperature and stirred for 24 hours. The solution was filtered, evaporated to dryness, and the residue chromatographed on silica gel eluting with ethyl acetate in dichloromethane to give an oil which crystallised on triturating with ether. The solid was recrystallised from ether and petrol to give the title compound (0.66 g) mp 110°-12° (dec).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated to dryness
  3. customthe residue chromatographed on silica gel eluting with ethyl acetate in dichloromethane
  4. customto give an oil which
  5. customcrystallised
  6. customon triturating with ether
  7. customThe solid was recrystallised from ether and petrol

Sources & evidence

ORD record
ord-d6eb3734523b4e898754f59c7337dcfd
Source dataset
uspto-grants-1990_09
Patent number
US04956378

Reaction notes

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