Acetic Acid → HCID 178441506, compound

HRID 2255547Notes

Reaction equation

HRID 2255547 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH2:16][CH2:17][CH3:18])[N:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:35]=[N:34][N:33]=3)=[CH:22][CH:21]=1)[C:8]2=[O:56])(=[O:3])[CH3:2].[NH4+].[OH-].C(O)(=O)C>CO.Cl>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH2:16][CH2:17][CH3:18])[N:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[NH:33][N:34]=[N:35][N:36]=3)=[CH:22][CH:21]=1)[C:8]2=[O:56])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 131718096HCID 131718096, compound

Product 1

HCID 178441506HCID 178441506, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.073 g (0.099 mmol) of the product from Example 42 in 2 mL of MeOH was added 4 drops of conc. HCl. The reaction mixture was stirred for 5 minutes and then made basic by addition of conc. NH4OH. The pH of the solution was adjusted to 5.0 by addition of acetic acid. The reaction mixture was concentrated in vacuo and the residue was taken up in 20 ml of EtOAc. The solution was washed with water (2×5 mL) and brine (1×5 mL) and dried over MgSO4. The mixture was filtered and concentrated in vacuo. The crude product was very insoluble and was consequently purified by trituration with CHCl3, EtOAc and hexanes to give 32 mg of an off white solid, 65% yield. 1H-NMR (CD3OD 300 MHz): 0.83 (t, 3H, J=7.3 Hz), 1.32 (m, 2H), 1.62 (2H, m), 2.09 (s, 2H), 2.68 (3 line m, 2H, J=8.1 Hz), 5.37 (bs, 2H), 7.00-7.10 (m, 4H), 7.42-7.61 (m, 5H), 7.89 (dd, 1H, J=2.4, 8.8 Hz), 8.39 (d, J=2.5 Hz). FABMS m/e: 494(M+ +1) calc. for C28H27N7O2.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washThe solution was washed with water (2×5 mL) and brine (1×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customwas consequently purified by trituration with CHCl3, EtOAc and hexanes
  7. customto give 32 mg of an off white solid, 65% yield

Sources & evidence

ORD record
ord-e7013da56d504e58ad7f26bd0842c990
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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