Ammonium Chloride → HCID 178522529, compound

HRID 1587480Notes

Reaction equation

HRID 1587480 reaction equation
[C:1]([CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:7][CH:6]([NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:5]1=[O:32])#[N:2].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:33]1[C:1]([CH2:3][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:7][CH:6]([NH:21][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:5]2=[O:32])=[N:2][N:35]=[N:34]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 9979758HCID 9979758, compound

Product 1

HCID 178522529HCID 178522529, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 150 mg of 1,3-dihydro-1-cyanomethyl-3-[(benzyloxycarbonyl)amino]-5-phenyl-2H-1,4-benzodiazepin-2-one, 124 mg of sodium azide, and 102 mg of ammonium chloride was heated in 3 ml of dry N,N-dimethylformamide at 110° C. for 4 hours. The reaction mixture was concentrated in vacuo and the residue was suspended in water, acidified with 1N HCl solution, and extracted twice with ethyl acetate. The combined organic extracts were dried (sodium sulfate) and concentrated to give 180 mg of crude product. Purification via preparative thick layer chromatography on 4 1.0 mm×20 cm×20 cm silica gel plates (90:10:1, chloroform-methanol-acetic acid elution) afforded 99 mg of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (sodium sulfate)
  4. concentrationconcentrated
  5. customto give 180 mg of crude product
  6. customPurification via preparative thick layer chromatography
  7. washon 4 1.0 mm×20 cm×20 cm silica gel plates (90:10:1, chloroform-methanol-acetic acid elution)

Sources & evidence

ORD record
ord-c89079795274436a8cc0e61403e4ef4e
Source dataset
uspto-grants-1993_06
Patent number
US05218114

Reaction notes

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