Dimethylformamide → HCID 178521750, compound

HRID 454684Notes

Reaction equation

HRID 454684 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].CN(C)C=O.[CH2:12]([O:19][C:20]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:39][C:21]=1[C:22]([NH:24][C:25]1[CH:26]=[C:27]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[CH:29][C:30]=1[C:31]#[N:32])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.C(Cl)(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:39][C:21]=1[C:22]([NH:24][C:25]1[CH:26]=[C:27]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[CH:29][C:30]=1[C:31]1[NH:32][N:3]=[N:2][N:1]=1)=[O:23])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium Chloride4×HCID 33557Sodium Azide4×HCID 66990791HCID 66990791, compound

Product 1

HCID 178521750HCID 178521750, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

Sodium azide (0.065 g) and ammonium chloride (0.053 g) were added to an N,N-dimethylformamide (2.5 mL) suspension of 2-(benzyloxy)-N-(4-cyanobiphenyl-3-yl)-5-(piperidin-1-yl)benzamide (0.25 g), followed by stirring at 110° C. for 2 hours. The reaction mixture was cooled to room temperature, and then sodium azide (0.065 g) and ammonium chloride (0.053 g) were added thereto, followed by stirring at 110° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then sodium azide (0.032 g) and ammonium chloride (0.026 g) were added thereto, followed by stirring at 110° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then sodium azide (0.032 g) and ammonium chloride (0.026 g) were added thereto, followed by stirring at 110° C. for 1 hour. The reaction mixture was cooled to room temperature, and then chloroform and water were added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] and then purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-93% chloroform/methanol] to obtain 0.18 g of 2-(benzyloxy)-N-(5-phenyl-2-(1H-tetrazol-5-yl)phenyl)-5-(piperidin-1-yl)benzamide as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring at 110° C. for 1 hour and 30 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. stirringby stirring at 110° C. for 1 hour and 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. stirringby stirring at 110° C. for 1 hour
  7. temperatureThe reaction mixture was cooled to room temperature
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]
  12. custompurified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-93% chloroform/methanol]

Sources & evidence

ORD record
ord-6f06526c6fae431bb65b9057f2d8c0af
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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