Triethylamine → HCID 15101030, compound

HRID 1587795Notes

Reaction equation

HRID 1587795 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]2[N:21]=[CH:22][C:23]([C:24]#[N:25])=[C:6]12)=[O:4].[N:26]1([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(CC)CC)C>O1CCCC1>[C:24]([C:23]1[CH:22]=[N:21][N:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)=[CH:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:29]3[CH2:28][CH2:27][N:26]([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])[CH2:31][CH2:30]3)[C:6]=12)#[N:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 643495Benzyl piperazine-1-carboxylateHCID 15100972HCID 15100972, compound

Product 1

HCID 15101030HCID 15101030, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6.3 g of 4-(chloroacetyl)-4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile, 4.2 g of 1-piperazinecarboxylic acid, phenylmethyl ester and 4.1 g of triethylamine in 250 ml of tetrahydrofuran was stirred under reflux for 18 hours, then cooled and filtered. The filtrate was evaporated, the residue taken up in chloroform, washed with water, dried, filtered and concentrated. The residual oil was triturated three times with ether:hexane (1:1), then with hexane. The solid was collected, washed with hexane and dried. The solid was heated to solution in 25 ml of ethyl acetate, filtered, diluted with 25 ml of hexane and cooled, giving 4.6 g of the desired product, mp 113°-115° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residual oil was triturated three times with ether:hexane (1:1)
  10. customThe solid was collected
  11. washwashed with hexane
  12. customdried
  13. temperatureThe solid was heated to solution in 25 ml of ethyl acetate
  14. filtrationfiltered
  15. additiondiluted with 25 ml of hexane
  16. temperaturecooled

Sources & evidence

ORD record
ord-13e9ea02df6e41e78817d3c22b9ef1cc
Source dataset
uspto-grants-1993_06
Patent number
US05219857

Reaction notes

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