Ammonium Chloride → HCID 58374675, compound

HRID 533176Notes

Reaction equation

HRID 533176 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:22]4[N:23]=[C:24]([NH:26][C:27]([CH:29]5[CH2:31][CH2:30]5)=[O:28])[N:25]=[C:21]4[CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+]>C(OCC)(=O)C>[N:2]1[NH:32][N:33]=[N:34][C:1]=1[C:3]1[N:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[N:22]4[N:23]=[C:24]([NH:26][C:27]([CH:29]5[CH2:30][CH2:31]5)=[O:28])[N:25]=[C:21]4[CH:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 44602526n-(5-(4-((6-Cyanopyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 58374675HCID 58374675, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of cyclopropanecarboxylic acid{5-[4-(6-cyano-pyridin-3-ylmethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide (143 mg, 0.35 mmol, 1 equiv), sodium azide (46 mg, 0.7 mmol, 2 equiv), ammonium chloride (38 mg, 0.7 mmol, 2 equiv) was stirred at 0° C. under nitrogen for 30 minutes. Afterwards the mixture was subjected for 100° C. for 16 hours. The crude of the reaction was diluted with ethyl acetate and washed with water. The organic phase was dried over MgSO4, filtered, and dried under vacuum. The crude was diluted with DMSO and submitted for preparative HPLC purification: HPLC system (XBridge™ Prep C18, 5 μm, 19×100 mm column); 8 min LC; flow: 20 mL/min; gradient: from 30% to 70% acetonitrile in water 0.1% TFA; to afford the final pure product (9 mg, 6% yield).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customdried under vacuum
  5. additionThe crude was diluted with DMSO
  6. customsubmitted for preparative HPLC purification
  7. custom8 min LC

Sources & evidence

ORD record
ord-1b063546c6a241ea9d39f9fde1f0a339
Source dataset
uspto-grants-2014_10
Patent number
US08853240B2

Reaction notes

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