Ammonium Chloride → HCID 178463672, compound

HRID 577769Notes

Reaction equation

HRID 577769 reaction equation
[CH:1]1([CH2:6][N:7]([CH2:33][CH3:34])[C:8]2[N:13]=[C:12]3[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][C:9]=2[CH2:19][N:20]([CH2:23][C:24]2[CH:29]=[C:28]([F:30])[C:27]([F:31])=[C:26]([F:32])[CH:25]=2)[C:21]#[N:22])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+].[N-:37]=[N+:38]=[N-:39].[Na+]>CN(C=O)C>[CH:1]1([CH2:6][N:7]([CH2:33][CH3:34])[C:8]2[N:13]=[C:12]3[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][C:9]=2[CH2:19][N:20]([CH2:23][C:24]2[CH:29]=[C:28]([F:30])[C:27]([F:31])=[C:26]([F:32])[CH:25]=2)[C:21]2[NH:39][N:38]=[N:37][N:22]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 57444436HCID 57444436, compound

Product 1

HCID 178463672HCID 178463672, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of [6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-ylmethyl-(3,4,5-trifluoro-benzyl)-cyanamide (0.280 g, 0.590 mmol) and ammonium chloride (0.160 g, 2.95 mmol) in dry DMF (10 mL) was added sodium azide (0.195 g, 2.95 mmol) and the reaction mixture was heated at 100° C. overnight. After the reaction mixture was cooled to RT, ice water was added, and this mixture was stirred for 30 min, and then extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over sodium sulfate and evaporated to yield the product as oil (90%).

Workup

  1. temperatureAfter the reaction mixture was cooled to RT
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-8dac4ccd9fc741848dfd5fc89ecebaa3
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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