Hydrochloric Acid → HCID 76577938, compound

HRID 240320Notes

Reaction equation

HRID 240320 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][O:6][N:7]=[C:8]1[C:20]2[C:15](=[N:16][C:17]([C:23](=[O:25])[NH2:24])=[C:18]([C:21]#[N:22])[N:19]=2)[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)C.O[Li].O.Cl>C1COCC1.O>[C:23]([C:17]1[N:16]=[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8](=[N:7][O:6][CH2:5][C:4]([OH:26])=[O:3])[C:20]2=[N:19][C:18]=1[C:21]#[N:22])(=[O:25])[NH2:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 76577927HCID 76577927, compound

Product 1

HCID 76577938HCID 76577938, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 37 (70 mg, 0.2 mmol) in THF/H2O (1:1, 15 ml) LiOH.H2O (41 mg, 1.0 mmol) was added and the mixture was stirred at room temperature. After 2 h 2N HCl was added up to pH=5. The solvent was removed under reduced pressure and the crude was purified by flash chromatography (CH2Cl2/MeOH/AcOH 90:10:1) affording 38 (41 mg, 63%) as yellow solid. ESI+MS: calcd for C15H9N5O4: 323.27; found: 324.3 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude was purified by flash chromatography (CH2Cl2/MeOH/AcOH 90:10:1)

Sources & evidence

ORD record
ord-11f0484324464553970db8b172e81968
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

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