Sodium Hydroxide → HCID 178504209, compound

HRID 1506256Notes

Reaction equation

HRID 1506256 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]2[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=[C:12]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:11]=23)[CH2:5][CH2:4]1.C(N(CC)C(C)C)(C)C.[C:39](N1C=CN=C1)(N1C=CN=C1)=[O:40].[OH-].[Na+]>CN(C)C(=O)C.O.C(#N)C>[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:10]3[C:11]4[CH:21]=[CH:20][N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:12]=4[N:13]=[CH:14][C:15]=3[C:16](=[O:17])[NH:18][C:39]2=[O:40])[CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 178504230HCID 178504230, compound

Product 1

HCID 178504209HCID 178504209, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

4-{[trans-4-(Hydroxymethyl)cyclohexyl]amino}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (270 mg, 0.645 mmol) in N,N-dimethylacetamide (3 mL) was mixed with N,N-diisopropylethylamine (3 mL) and 1,1′-carbonyldiimidazole (1.04 g, 6.45 mmol) and stirred at 120° C. for 3 hours. The reaction mixture was allowed to cool to room temperature and stirred with 1M aqueous sodium hydroxide (3 mL) and acetonitrile (3 mL) for 5 hours. After addition of water, the reaction mixture was 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 (ethyl acetate/hexane=9/1 (v/v)) to give the title compound as a colorless solid (206 mg, yield 73%).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=9/1 (v/v))

Sources & evidence

ORD record
ord-b3b36cbe51834e7b812d030831cd448d
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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