Ammonium Chloride → HCID 71258209, compound

HRID 1506216Notes

Reaction equation

HRID 1506216 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH:16][CH:17]=O)=[O:15])=[CH:12][N:11]=[C:10]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>CN1CCCC1=O>[CH:1]1([N:7]2[C:8]3[C:9]4[CH:21]=[CH:20][N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:28])([CH3:27])[CH3:29])[C:10]=4[N:11]=[CH:12][C:13]=3[C:14](=[O:15])[N:16]=[CH:17]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 86726636HCID 86726636, compound

Product 1

HCID 71258209HCID 71258209, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-(Cyclohexylamino)-N-formyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (12.4 mg, 0.0311 mmol) in N-methyl-2-pyrrolidinone (0.5 mL) was stirred at 200° C. for 30 minutes under microwave irradiation. The reaction mixture was allowed to cool to room temperature and, after addition of saturated aqueous ammonium chloride, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)) to give the title compound as a pale yellow amorphous (9.2 mg, yield 74%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-43731ace86af43a0b3913bdba1a2a689
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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