Water → HCID 11594915, compound

HRID 2092183Notes

Reaction equation

HRID 2092183 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([NH:12][C:13]([NH:15][C:16]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:17]=2[CH:18]=[N:19][N:20]3C(OC)=O)=[O:14])[CH2:4][CH2:3]1.O>[OH-].[Na+].CO>[NH:20]1[C:21]2[C:17](=[C:16]([NH:15][C:13]([NH:12][CH:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[N:2]([CH3:1])[CH2:3][CH2:4]3)=[O:14])[CH:24]=[CH:23][CH:22]=2)[CH:18]=[N:19]1

Participants

5

Reactant 2

HCID 962WaterHCID 11710626HCID 11710626, compound

Product 1

HCID 11594915HCID 11594915, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The compound obtained in example 95B was dissolved in 2 mls of 5N NaOH in methanol and stirred for 2 hours at ambient temperature. Water was added to the reaction mixture and the precipitate was collected. The precipitated compound was redissolved in 10% methanol in dichloromethane and purified by flash chromatography on silica using a gradient from dichloromethane to 20% methanol in dichloromethane with a few drops of NH4OH as the solvents to provide the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.99 (s, 1 H) 8.53 (s, 1 H) 8.01 (s, 1 H) 7.70 (d, J=7.46 Hz, 1 H) 7.21 (t, J=7.97 Hz, 1 H) 7.11-7.17 (m, 2 H) 7.07 (t, J=8.48 Hz, 1 H) 6.58-6.72 (m, 3 H) 4.76-4.85 (m, 1H) 3.15-3.29 (m, 2 H) 2.89 (s, 3 H) 1.99 (s, 2 H). MS (DCI/NH3) m/z 322.0 (M+H)+.

Workup

  1. customthe precipitate was collected
  2. dissolutionThe precipitated compound was redissolved in 10% methanol in dichloromethane
  3. custompurified by flash chromatography on silica using a gradient from dichloromethane to 20% methanol in dichloromethane with a few drops of NH4OH as the solvents

Sources & evidence

ORD record
ord-ad84f131760947e1932e0f837b8cbea8
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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