Benzylamine → HCID 18917585, compound

HRID 1291756Notes

Reaction equation

HRID 1291756 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[C:19]([CH3:22])=[N:20][N:21]=[C:11]3[CH:10](NNC(NN)=O)[N:9]=2)=[CH:4][CH:3]=1.Cl.[O:30]1[CH2:35]COCC1.N(OCCC(C)C)=O.[CH2:44]([NH2:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C)C=O.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:44]([NH:51][C:35]([CH:10]1[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]2[C:19]([CH3:22])=[N:20][N:21]=[C:11]12)=[O:30])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8053Isoamyl NitriteHCID 18917679HCID 18917679, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 18917585HCID 18917585, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (±)-[6-(4-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]carbohydrazide (109.7 mg) in dimethylformamide (1 ml) was cooled to -40° C. and 4N dioxane hydrochloride (0.23 ml) was added thereto. The temperature of the mixture was raised to 0° C. The reaction mixture was cooled again to -40° C. and isopentyl nitrite (40 μl) was added thereto. The mixture was stirred at -30° C. for 1 hour. The temperature of the mixture was again cooled to -70° C. Triethylamine (0.125 ml) was added to the mixture and 10 minutes later, benzyl amine (77 μl) was added thereto. Then, the temperature of the mixture was raised to 0° C. and the mixture was stirred for 3 hours. The mixture was stirred at room temperature for 10 hours. Dimethylformamide was distilled away under reduced pressure and the residue obtained was dissolved in chloroform and washed with 0.3N hydrochloric acid, an aqueous solution of sodium bicarbonate and water in order and dried over anhydrous sodium sulfate. Chloroform was distilled away under reduced pressure and ethyl acetate was added to the residue to give 95.1 mg of (±)-N-benzyl-[6-(4-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepin-4-yl]carboxamide as colorless needle crystals, mp. 265°-267° C.

Workup

  1. temperatureThe reaction mixture was cooled again to -40° C.
  2. temperatureThe temperature of the mixture was again cooled to -70° C
  3. temperatureThen, the temperature of the mixture was raised to 0° C.
  4. stirringthe mixture was stirred for 3 hours
  5. stirringThe mixture was stirred at room temperature for 10 hours
  6. distillationDimethylformamide was distilled away under reduced pressure
  7. customthe residue obtained
  8. washwashed with 0.3N hydrochloric acid
  9. dry with materialan aqueous solution of sodium bicarbonate and water in order and dried over anhydrous sodium sulfate
  10. distillationChloroform was distilled away under reduced pressure and ethyl acetate
  11. additionwas added to the residue

Sources & evidence

ORD record
ord-09d5e08d9868431a88a153fac0981dfb
Source dataset
uspto-grants-1998_05
Patent number
US05753649

Reaction notes

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