Sulfuric Acid → HCID 86670151, compound

HRID 2169607Notes

Reaction equation

HRID 2169607 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:14]=3[C:15]#[N:16])[CH2:7][CH:6]3[CH2:22][O:23][CH2:24][CH2:25][N:5]3[C:4]=2[N:3]=1.S(=O)(=O)(O)[OH:27]>CCOC(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:14]=3[C:15]([NH2:16])=[O:27])[CH2:7][CH:6]3[CH2:22][O:23][CH2:24][CH2:25][N:5]3[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86670149HCID 86670149, compound

Product 1

HCID 86670151HCID 86670151, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 20 mL round-bottomed flask charged with 2-((2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)methyl)-4-methylbenzonitrile (PREPARATION x83, 52 mg, 0.146 mmol) was added sulfuric acid (1.6 mL, 29.2 mmol). The resulting yellow solution was stirred overnight at room temperature and was subsequently diluted with EtOAc and washed with saturated NaHCO3 to adjust the pH to ˜8. The combined organic layers were dried over MgSO4, filtered, and concentrated to give an orange solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.88-3.02 (m, 5 H), 3.09-3.18 (m, 3 H), 3.19-3.28 (m, 2 H), 3.41-3.51 (m, 3 H), 3.59-3.71 (m, 2 H), 3.80-3.91 (m, 3 H), 3.91-4.00 (m, 2 H), 4.19-4.29 (m, 3 H), 4.30-4.58 (m, 2 H), 7.16-7.29 (m, 10 H), 7.37-7.45 (m, 2 H), 7.73-7.82 (m, 2 H); ESI-MS m/z [M+H]+ calc'd for C18H20ClN5O2, 374.1; found 374.2.

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an orange solid, which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-2cc35bd8f87848749a0e3489725ab6b4
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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