Hydrochloric Acid → HCID 76577936, compound

HRID 240323Notes

Reaction equation

HRID 240323 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][NH:6][C:7](=[O:29])[CH2:8][O:9][N:10]=[C:11]1[C:23]2[C:18](=[N:19][C:20]([C:26](=[O:28])[NH2:27])=[C:21]([C:24]#[N:25])[N:22]=2)[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2)C.O[Li].O.Cl>C1COCC1.O>[C:26]([C:20]1[N:19]=[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11](=[N:10][O:9][CH2:8][C:7]([NH:6][CH2:5][C:4]([OH:30])=[O:3])=[O:29])[C:23]2=[N:22][C:21]=1[C:24]#[N:25])(=[O:28])[NH2:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 76577930HCID 76577930, compound

Product 1

HCID 76577936HCID 76577936, compoundYield 70.1%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
0 °C

Procedure

To a solution of 40 (60 mg, 0.15 mmol) in THF/H2O (1:1, 15 ml) LiOH.H2O (30 mg, 0.71 mmol) was added. The mixture was stirred at room temperature and after 2 h 2N HCl was added up to pH=5. The solvent was removed under reduced pressure and a 1:1 mixture of CH2Cl2/MeOH (10 ml) was added. The solution was cooled at 0° C. and the precipitate was collected by filtration, affording 41 (40 mg, 70%) as green solid. 1H NMR (300 MHz, DMSO d6+TFA): δ 8.35 (t, 1H), 8.13 (dd, 1H), 7.91 (m, 2H), 7.78 (ddd, 1H), 4.92 (s, 2H), 3.87 (d, 2H). ESI+MS: calcd for C17H12N6O5: 380.32; found: 381.4 (MH+).

Workup

  1. additionwas added up to pH=5
  2. customThe solvent was removed under reduced pressure
  3. additiona 1:1 mixture of CH2Cl2/MeOH (10 ml)
  4. additionwas added
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b9e0d2f3228242f5a9236c42a902e158
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

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