Ammonium Hydroxide → HCID 89498109, compound

HRID 1430265Notes

Reaction equation

HRID 1430265 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([I:14])[CH:10]=[C:9]1[C:15]([OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:20]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([I:14])[CH:10]=[C:9]1[C:15]([NH2:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 89497880HCID 89497880, compound

Product 1

HCID 89498109HCID 89498109, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 129A (450 mg) in tetrahydrofuran (12 mL) at 0° C. was added carbonyldiimidazole (642 mg). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was cooled to 0° C. and ammonium hydroxide (3 mL) was added. The mixture was stirred at room temperature for 2 hours and concentrated. The residue was dissolved in ethyl acetate, washed with brine and concentrated to provide the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-06202e4ec02b4ffdb3fede67ca248e35
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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