Ammonia → HCID 13747410, compound

HRID 1587084Notes

Reaction equation

HRID 1587084 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH2:12]([O:14][C:15]1[CH:20]=[C:19]([CH2:21][C:22]([NH:24][CH:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH2:26][CH2:27][CH3:28])=[O:23])[CH:18]=[CH:17][C:16]=1[CH2:41][CH2:42][C:43]([NH2:45])=O)[CH3:13].C(O)(=O)CC.C(N1C=CN=C1)(N1C=CN=C1)=O.N>O1CCCC1.O.N1C=CC=CC=1>[CH2:12]([O:14][C:15]1[CH:20]=[C:19]([CH2:21][C:22]([NH:24][CH:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH2:26][CH2:27][CH3:28])=[O:23])[CH:18]=[CH:17][C:16]=1[CH2:41][CH2:42][C:43]#[N:45])[CH3:13]

Participants

9

Reactant 5

HCID 222Ammonia2×HCID 1032Propionic AcidHCID 73974-Toluenesulfonyl chlorideHCID 682631,1'-CarbonyldiimidazoleHCID 54545719HCID 54545719, compound

Product 1

HCID 13747410HCID 13747410, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

At ambient temperature, p-toluenesulphonic acid chloride (45.8 mg, 0.24 mmol) is added to a mixture of 3-[2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-phenyl]-propionic acid amide, (56 mg, 0.12 mmol) melting point 153°-155° C. [prepared from the corresponding propionic acid by reacting with carbonyldiimidazole and then with ammonia in tetrahydrofuran] and absolute pyridine (0.044 ml). The mixture is stirred for 45 minutes at 20° C. and for 2 hours at 50° to 60° C. After cooling, water is added, the mixture is made alkaline with concentrated ammonia and extracted three times with chloroform. The combined chloroform extracts are washed with water, dried over sodium sulphate, filtered and concentrated evaporation in vacuo. The evaporation residue is purified by column chromatography on silica gel (chloroform/ethyl acetate=9/1).

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with chloroform
  3. washThe combined chloroform extracts are washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customevaporation in vacuo
  8. customThe evaporation residue is purified by column chromatography on silica gel (chloroform/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-5c3ab60d68da4acd8381f2d907bbb6ec
Source dataset
uspto-grants-1993_06
Patent number
US05216167

Reaction notes

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