Ammonium Hydroxide → HCID 89498250, compound

HRID 336584Notes

Reaction equation

HRID 336584 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=O)[NH:5][C:6]=1[CH3:7].C(N1C=CN=C1)([N:13]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:13])=[O:10])[NH:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 89498152HCID 89498152, compound

Product 1

HCID 89498250HCID 89498250, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 23B (7.7 g) in tetrahydrofuran (20 mL) at 0° C. was added carbonyldiimidazole (14.9 g). 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-794df0bb6d114c6a8be71624335e0b83
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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