Ammonium Chloride → HCID 66665612, compound

HRID 872337Notes

Reaction equation

HRID 872337 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][N:21]4[C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[N-:36]=[N+:37]=[N-:38].[Na+].[NH4+].[Cl-].C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[C:24]([C:26]5[N:36]=[N:37][NH:38][N:27]=5)[CH:23]=[CH:22][N:21]4[C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 66665217HCID 66665217, compound

Product 1

HCID 66665612HCID 66665612, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of {1-[4-(7-cyano-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (200 mg, 0.43 mmol), sodium azide (336 mg, 5.16 mmol, 12 equiv), NH4Cl (276 mg, 5.16 mmol, 12 equiv) and DMF (4.3 mL) was heated under an argon atmosphere for 3.5 h at 150° C. in a microwave apparatus. The reaction mixture was added to a saturated aqueous NaHCO3 solution (10 mL). The resulting mixture was extracted with a 4:1 CH2Cl2/isopropanol mixture (25 mL). The combined organic phases were dried (Na2SO4 anh), and concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera; 25 g SNAP cartridge: 80% hexane/20% EtOAc for 3.0 min., gradient to 70% hexane/30% EtOAc over 13.7 min.) to give (1-{4-[3-Phenyl-7-(2H-tetrazol-5-yl)-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (0.12 g, 52%):

Workup

  1. extractionThe resulting mixture was extracted with a 4:1 CH2Cl2/isopropanol mixture (25 mL)
  2. dry with materialThe combined organic phases were dried (Na2SO4 anh)
  3. concentrationconcentrated under reduced pressure
  4. customThe remaining material was purified
  5. customMPLC (Biotage Isolera; 25 g SNAP cartridge: 80% hexane/20% EtOAc for 3.0 min., gradient to 70% hexane/30% EtOAc over 13.7 min.)

Sources & evidence

ORD record
ord-5c44910762bb45588eb482ef24ab637e
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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