Ammonium Chloride → HCID 178426906, compound

HRID 558969Notes

Reaction equation

HRID 558969 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[CH3:7][C:8]1[CH:32]=[C:31]([C:33]([N:35]2[CH2:41][CH2:40][CH2:39][CH2:38][C:37]3[CH:42]=[CH:43][CH:44]=[CH:45][C:36]2=3)=[O:34])[CH:30]=[CH:29][C:9]=1[CH2:10][NH:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[F:24])[N:17]([CH2:25][C:26]#[N:27])[C:16](=[O:28])[CH2:15]1)=[O:13]>CN(C=O)C>[CH3:7][C:8]1[CH:32]=[C:31]([C:33]([N:35]2[CH2:41][CH2:40][CH2:39][CH2:38][C:37]3[CH:42]=[CH:43][CH:44]=[CH:45][C:36]2=3)=[O:34])[CH:30]=[CH:29][C:9]=1[CH2:10][NH:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[F:24])[N:17]([CH2:25][C:26]2[NH:27][N:3]=[N:2][N:1]=2)[C:16](=[O:28])[CH2:15]1)=[O:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 115844924-Cyanomethyl-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide

Product 1

HCID 178426906HCID 178426906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (78 mg, 1.2 mmol) and ammonium chloride (21 mg, 0.40 mmol) were added to a solution of 4-cyanomethyl-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide from Example 13 (210 mg, 0.40 mmol) in DMF (5 ml) and the mixture was stirred at 100° C. for 18 h. The mixture was cooled and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant CHCl3 100% to CHCl3:methanol;triethylamine 97:2:1 to CHCl3:methanol;triethylamine 94:4:2). The product was partitioned between chloroform and potassium hydrogen sulphate, separated and the organic phase was dried and evaporated in vacuo; yield 33 mg, 15%.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated in vacuo
  3. customThe residue was purified by flash chromatography on silica (eluant CHCl3 100% to CHCl3:methanol;triethylamine 97:2:1 to CHCl3:methanol;triethylamine 94:4:2)
  4. customThe product was partitioned between chloroform and potassium hydrogen sulphate
  5. customseparated
  6. customthe organic phase was dried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-8f6b48b1178a430aaba52428b526211f
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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