Triethylamine → HCID 14722605, compound

HRID 1638648Notes

Reaction equation

HRID 1638648 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=[O:42])[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:16]([C:39]([NH2:41])=[O:40])[CH2:15]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:50](Cl)(=[O:53])[CH2:51][CH3:52]>ClC(Cl)Cl>[C:1]([C:4]1[CH:9]=[C:8]([NH:10][C:50](=[O:53])[CH2:51][CH3:52])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=[O:42])[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:16]([C:39]([NH2:41])=[O:40])[CH2:15]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 14722598HCID 14722598, compound

Product 1

HCID 14722605HCID 14722605, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 4.5 parts of N-(2-acetyl-4-aminophenyl)-3-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide in 60 parts of trichloromethane were added 1.17 parts of N,N-diethylethanamine. A solution of 0.78 parts of propanoyl chloride in 45 parts of trichloromethane was added dropwise at room temperature (slightly exothermic reaction, the temperature rose from 24° C. to 30° C.). Upon completion, the whole was stirred for 3 hours at room temperature. The separated organic layer was washed with a sodium carbonate solution in water and water, dried, filtered and evaporated. The residue was crystallized from acetonitrile. After cooling to 0° C., the product was filtered off and dried in vacuo, first at 50° C. and then at 100° C., yielding 2.93 parts (57.7%) of N-[2-acetyl-4-[(1-oxopropyl)amino]phenyl]-3(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide; mp. 163.4° C. (compound 32).

Workup

  1. customslightly exothermic reaction
  2. customrose from 24° C. to 30° C.
  3. washThe separated organic layer was washed with a sodium carbonate solution in water and water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from acetonitrile
  8. temperatureAfter cooling to 0° C.
  9. filtrationthe product was filtered off
  10. customdried in vacuo, first at 50° C.

Sources & evidence

ORD record
ord-3ed725f53b534758ad5181c3eb017878
Source dataset
uspto-grants-1989_11
Patent number
US04880808

Reaction notes

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