Water → HCID 136027595, compound

HRID 1428852Notes

Reaction equation

HRID 1428852 reaction equation
O.[OH-].[Li+].O.C([O:7][C:8]([C:10]1[CH:11]=[N:12][N:13]([C:15]2[NH:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][C:19]4[O:29][CH2:28][CH2:27][O:26][C:20]=4[CH:21]=3)[N:16]=2)[CH:14]=1)=[O:9])C>C1COCC1>[O:25]=[C:23]1[C:22]2[C:17](=[CH:18][C:19]3[O:29][CH2:28][CH2:27][O:26][C:20]=3[CH:21]=2)[N:16]=[C:15]([N:13]2[CH:14]=[C:10]([C:8]([OH:9])=[O:7])[CH:11]=[N:12]2)[NH:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 136337177HCID 136337177, compound

Product 1

HCID 136027595HCID 136027595, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (28.7 mg, 0.684 mmol) and water (0.29 mL) were added to 1-(4-oxo-3,4,7,8-tetrahydro-[1,4]dioxino[2,3-g]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (78.0 mg, 0.228 mmol) in THF (0.85 mL). The reaction mixture was stirred at room temperature for 18 h and was then concentrated and the residue re-dissolved in water (5 mL). This solution was brought to pH 1 with 1M aqueous HCl. The resulting precipitate was collected and dried to yield the titled compound (54.3 mg, 75% yield). MS (ESI/Cl): mass calcd. for C14H10N4O5, 314.1; m/z found, 315.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.97 (s, 1H), 12.61 (s, 1H), 8.89 (d, J=0.6 Hz, 1H), 8.23 (s, 1H), 7.48 (s, 1H), 7.14 (s, 1H), 4.46-4.29 (m, 4H).

Workup

  1. concentrationwas then concentrated
  2. dissolutionthe residue re-dissolved in water (5 mL)
  3. customThe resulting precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-786f292f29dc4a7f980ccac0cb7ba2c6
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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