Sodium Chloride → HCID 86726637, compound

HRID 1506235Notes

Reaction equation

HRID 1506235 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([C:21]([NH2:23])=[O:22])=[CH:19][N:18]=[C:17]3[N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=[CH:26][C:16]=23)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35](N1C=CN=C1)(N1C=CN=C1)=[O:36].[Cl-].[Na+]>CN(C)C(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[C:16]4[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:17]=4[N:18]=[CH:19][C:20]=3[C:21](=[O:22])[NH:23][C:35]2=[O:36])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 71264268HCID 71264268, compound

Product 1

HCID 86726637HCID 86726637, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-[(1-Benzylpiperidin-4-yl)amino]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (484 mg, 1.01 mmol) in N,N-dimethylacetamide (5 mL) was stirred with 1,1′-carbonyldiimidazole (486 mg, 3.00 mmol) at 120° C. for 3 hours. The reaction mixture was allowed to cool to room temperature and, after addition of saturated aqueous sodium 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 (chloroform/methanol=20/1 (v/v)) to give the title compound as a colorless solid (360 mg, yield 70%).

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 (chloroform/methanol=20/1 (v/v))

Sources & evidence

ORD record
ord-b9434a54d157409297ae715a2a28697c
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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