Water → HCID 57588081, compound

HRID 1952016Notes

Reaction equation

HRID 1952016 reaction equation
[CH2:1]([NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=O)=[CH:8][CH:7]=1)[CH:2]([CH3:4])[CH3:3].NN.[OH-].[K+].O>C(O)CO>[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[CH:10][N:11]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 57595758HCID 57595758, compound

Product 1

HCID 57588081HCID 57588081, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
180 °C

Procedure

To (6-Isobutylamino-pyridin-3-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (P-0025, 60.0 mg, 0.20 mmol, prepared as described in Example 5) in 1,2-ethanediol (5.0 mL) was added hydrazine (1.0 mL, 0.032 mol) and potassium hydroxide (200.0 mg, 3.56 mmol). The reaction mixture was heated to 180° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography eluting with 10% methanol in dichloromethane to give compound (P-0028, 10 mg, 16.7%). MS (ESI) [M+H+]+=281.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 10% methanol in dichloromethane
  7. customto give compound (P-0028, 10 mg, 16.7%)

Sources & evidence

ORD record
ord-f1ba566edc89498694765da39a6a23ab
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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