Sulfuric Acid → HCID 86670096, compound

HRID 2169549Notes

Reaction equation

HRID 2169549 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, 2 H), 3.10-3.19 (m, 1 H), 3.22-3.29 (m, 1 H), 3.44-3.49 (m, 1 H), 3.63-3.73 (m, 1 H), 3.81-3.99 (m, 2 H), 4.21-4.29 (m, 1 H), 4.36-4.61 (m, 2 H), 7.19-7.24 (m, 1 H), 7.30-7.50 (m, 5 H), 7.78-7.87 (m, 1 H). 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-dabbd1250251447da7c4f505bc61dd22
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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