Sulfuric Acid → HCID 86670096, compound

HRID 1631711Notes

Reaction equation

HRID 1631711 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]#[N:16])[CH2:7][CH:6]3[CH2:21][O:22][CH2:23][CH2:24][N:5]3[C:4]=2[N:3]=1.S(=O)(=O)(O)[OH:26]>C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]([NH2:16])=[O:26])[CH2:7][CH:6]3[CH2:21][O:22][CH2:23][CH2:24][N:5]3[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86670097HCID 86670097, compound

Product 1

HCID 86670096HCID 86670096, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-((2-Chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)methyl)benzonitrile (PREPARATION x17, 140 mg, 0.410 mmol) was dissolved in concentrated sulfuric acid (1 mL) and was stirred overnight at room temperature. Following reaction, the mixture was diluted with ethyl acetate and was washed with aqueous saturated NaHCO3 (2×15 mL) and brine (2×5 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated. The product was purified by LC/MS using a gradient of 20-45% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). The pure fractions were combined and lyophilized to afford the title compound as a white solid (147 mg, 99%). 1H NMR (400 MHz, DMSO-d6) δ 2.91-3.05 (m, 2H), 3.10-3.19 (m, 1H), 3.22-3.29 (m, 1H), 3.44-3.49 (m, 1H), 3.63-3.73 (m, 1H), 3.81-3.99 (m, 2H), 4.21-4.29 (m, 1H), 4.36-4.61 (m, 2H), 7.19-7.24 (m, 1H), 7.30-7.50 (m, 5H), 7.78-7.87 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C17H18ClN5O2, 360.11. found 360.2.

Workup

  1. customreaction
  2. washwas washed with aqueous saturated NaHCO3 (2×15 mL) and brine (2×5 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by LC/MS

Sources & evidence

ORD record
ord-fdd74930fbe9455dbe15ec14435bb13b
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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