Hydrochloric Acid → HCID 66851217, compound

HRID 1466556Notes

Reaction equation

HRID 1466556 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[NH:14]C(=O)OC(C)(C)C)[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[NH2:14])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66850645HCID 66850645, compound

Product 1

HCID 66851217HCID 66851217, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 5-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-ylcarbamate (774 mg, 2.29 mmol, 1 eq) was added hydrogen chloride (6.0 mL of a 4.0M solution in 1,4-dioxane, 24 mmol, 10 eq). The reaction mixture was stirred at room temperature for 4 hours and then evaporated to dryness. The solid residue was partitioned between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The aqueous portion was extracted once more with dichloromethane, and the combined organic extracts dried over magnesium sulfate and concentrated to give 5-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-amine, which was carried forward without purification. LCMS (ESI) m+H=238.3; 1H NMR (400 MHz, CDCl3) δ: 7.35 (d, 1H), 7.22 (overlapping s and s, 2H), 6.94 (d, 1H), 3.83 (s, 3H), 3.70 (d, 2H), 3.66 (s, 3H).

Workup

  1. customevaporated to dryness
  2. customThe solid residue was partitioned between dichloromethane
  3. extractionThe aqueous portion was extracted once more with dichloromethane
  4. dry with materialthe combined organic extracts dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-88186b8ef8004e02b05f17400cff95f6
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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