Dimethylformamide → HCID 67152754, compound

HRID 1783588Notes

Reaction equation

HRID 1783588 reaction equation
[NH4+].[Cl-].[C:3]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:31])[C:18]([C:20]2[C:28]3[C:23](=[N:24][C:25](C#N)=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C@H:13]([CH3:32])[CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N-:33]=[N+:34]=[N-:35].[Na+].[CH3:37][N:38](C=O)C>>[C:3]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:31])[C:18]([C:20]2[C:28]3[C:23](=[N:24][C:25]([N:33]4[CH:37]=[N:38][N:35]=[N:34]4)=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C@H:13]([CH3:32])[CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 5495817HCID 5495817, compound

Product 1

HCID 67152754HCID 67152754, compound

Procedure

An excess of NH4Cl (27 mg) was added into a solution of 1-(benzoyl)-3-(R)-methyl-4-[(6-cyano-7-azaindol-3-yl)-oxoacetyl]piperazine (20 mg) and NaN3 (16 mg) in DMF. The reaction was heated to reflux for 12 h. After cooling down, the mixture was concentrated under reduced pressure and the residue was purified using Shimadzu automated preparative HPLC System to give 1-benzoyl-3-(R)-methyl-4-[(6-(tetrazol-1-yl)-7-azaindol-3-yl)-oxoacetyl]piperazine (6.3 mg). MS m/z: (M+H)+ Calc'd for C22H21N8O3: 445.17; Found 3445.16. HPLC retention time: 1.42 minutes (column B); Column B: PHX-LUNA C18 4.6×30 mm.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 12 h
  3. temperatureAfter cooling down
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customthe residue was purified

Sources & evidence

ORD record
ord-9e6e9d37612648bdb4e1a0138a1f96c2
Source dataset
uspto-grants-2009_03
Patent number
US07501420B2

Reaction notes

Loading…