Hydrochloric Acid → HCID 25234703, compound

HRID 1924456Notes

Reaction equation

HRID 1924456 reaction equation
[C:1]([C:5]1[C:6]([O:39][CH3:40])=[C:7]([CH:28]=[C:29]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[CH:30]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][C:11]=1[CH2:21][NH:22][CH2:23][CH2:24]C(C)C)([CH3:4])([CH3:3])[CH3:2].C(C=O)=O.[NH4+:45].[OH-].Cl>CCO>[C:1]([C:5]1[C:6]([O:39][CH3:40])=[C:7]([CH:28]=[C:29]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[CH:30]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][C:11]=1[C:21]1[NH:45][CH:24]=[CH:23][N:22]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7860GlyoxalHCID 14923Ammonium HydroxideHCID 25234711HCID 25234711, compound

Product 1

HCID 25234703HCID 25234703, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product from Example 30, Part A (50 mg, 0.10 mmol) in EtOH (2 ml) was added glyoxal (57 uL, 0.50 mmol) and concentrated aqueous NH4OH (70 uL, 0.50 mmol). The resulting mixture was stirred at room temperature for 16 h. To the mixture was added 1 N aq. HCl until pH=7, and the mixture was partitioned between H2O (10 ml) and EtOAc (2×10 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 5% MeOH in CH2Cl2 as the eluent to give the title compound (27 mg, 50%). 1H NMR (300 MHz, DMSO-d6) δ 12.39 (s, 1 H) 11.40 (d, J=1.84 Hz, 1 H) 9.98 (s, 1 H) 7.89 (d, J=8.82 Hz, 1 H) 7.66-7.76 (m, 2 H) 7.38 (t, J=2.21 Hz, 2 H) 7.23-7.31 (m, 2 H) 7.06-7.21 (m, 3 H) 5.63 (dd, J=8.09, 1.84 Hz, 1 H) 3.78 (s, 3 H) 3.07 (s, 3 H) 1.37 (s, 9 H).

Workup

  1. customthe mixture was partitioned between H2O (10 ml) and EtOAc (2×10 ml)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel using 5% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-a53964202a1043829f8ae4b0cdc40ef5
Source dataset
uspto-grants-2012_05
Patent number
US08178548B2

Reaction notes

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