Potassium Hydroxide → HCID 136027634, compound

HRID 1428851Notes

Reaction equation

HRID 1428851 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:13]2[NH:26][C:25](=[O:27])[C:24]3[C:15](=[C:16]4[C:21](=[CH:22][CH:23]=3)[O:20][CH2:19][CH2:18][O:17]4)[N:14]=2)[CH:12]=1)=[O:7])C>C1COCC1>[O:27]=[C:25]1[C:24]2[C:15](=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH2:18][O:17]3)[N:14]=[C:13]([N:11]2[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[N:10]2)[NH:26]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 136337175HCID 136337175, compound

Product 1

HCID 136027634HCID 136027634, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous potassium hydroxide (1M, 2.6 mL, 2.6 mmol) was added to 1-(8-oxo-2,3,7,8-tetrahydro-1,4-dioxa-5,7-diaza-phenanthren-6-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.298, 0.869 mmol) in THF (2.6 mL). The reaction mixture was allowed to stir at room temperature for 2 days and was then concentrated. The residue was redissolved in water (10 mL) and brought to pH 1 with 1M aqueous HCl. The resulting precipitate was collected by filtration to yield the titled compound (0.235 g, 85% yield). MS (ESI/Cl): mass calcd. for C14H10N4O5, 314.1; m/z found, 315.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 13.01 (s, 1H), 12.73 (s, 1H), 8.86 (d, J=0.7 Hz, 1H), 8.24 (d, J=0.6 Hz, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.05 (d, J=8.7 Hz, 1H), 4.40 (s, 4H).

Workup

  1. concentrationwas then concentrated
  2. dissolutionThe residue was redissolved in water (10 mL)
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-7b4dcb2013124ece85169d847818163a
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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