Triethylamine → HCID 15101030, compound

HRID 893657Notes

Reaction equation

HRID 893657 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-146f18f5e16c4ab9a059af2d5eea9027
Source dataset
uspto-grants-1992_06
Patent number
US05126340

Reaction notes

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