Sulfuric Acid → HCID 86680019, compound

HRID 1915813Notes

Reaction equation

HRID 1915813 reaction equation
[CH3:1][C:2]1(O)[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.[OH-:24].[K+].[C:26](#[N:28])[CH3:27]>>[CH3:1][C:2]1([NH:28][C:26](=[O:24])[CH3:27])[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 86679984HCID 86679984, compound

Product 1

HCID 86680019HCID 86680019, compoundYield 93%

Procedure

4-Methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-ol (610 mg, 2.40 mmol) was dissolved in acetonitrile (4 mL) and cooled to 0° C. before concentrated sulphuric acid (2.1 mL) was added dropwise. The reaction was allowed to warm to room temperature and stirred for 1 hr before being poured onto ice (150 g), basified with KOH and extracted with DCM (2×30 mL). The combined organic layers were washed with brine (20 mL), passed through a phase separation cartridge and concentrated under reduced pressure to give N-(4-methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide as a yellow solid (660 mg, 93%). 1H NMR (400 MHz, CDCl3) δ 8.05-7.98 (m, 1H), 5.31 (s, 1H), 3.81-3.73 (m, 3H), 3.35 (ddd, J=14.2, 9.3, 2.2 Hz, 1H), 3.22 (t, J=5.9 Hz, 2H), 3.09 (ddd, J=14.2, 7.6, 2.5 Hz, 1H), 2.43-2.31 (m, 2H), 2.05-1.95 (m, 3H), 1.89-1.74 (m, 4H), 1.53-1.36 (m, 3H).

Workup

  1. additionwas added dropwise
  2. additionbefore being poured onto ice (150 g)
  3. extractionextracted with DCM (2×30 mL)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. custompassed through a phase separation cartridge
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-914e58ff16804a68ad061060f09c96b9
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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