Hydrochloric Acid → HCID 178516366, compound

HRID 348023Notes

Reaction equation

HRID 348023 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[N:10][N:11]3[C:16]([O:17]CC)=[CH:15][CH:14]=[N:13][C:12]=23)=[CH:4][CH:3]=1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[N:10][N:11]3[C:16]([OH:17])=[CH:15][CH:14]=[N:13][C:12]=23)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 2723671Tetrabutylammonium HydroxideHCID 10091401HCID 10091401, compound

Product 1

HCID 178516366HCID 178516366, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-ethoxypyrazolo[1,5-a]pyrimidine (11A-1; 250 mg, 0.653 mmol) in THF (6.5 ml) was added water (1.5 ml) and 1M tetrabutylammonium hydroxide in water (3.3 ml, 3.3 mmol). The reaction was heated at 60° C. overnight, cooled, diluted with ethyl acetate and water, and then adjusted to pH 4.5 with 1M aqueous HCl. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated to afford, after trituration from ethyl acetate, I-12A-1a as a tan solid (138 mg, 60%): +APcI MS (M+1) 354.1; 1H NMR (400 MHz, CD3OD) δ 7.79 (d, J=7.1 Hz, 1H), 7.49–7.43 (m, 1H), 7.42–7.35 (m, 3H), 7.30 (d, J=8.7 Hz, 2H), 7.15 (d, J=8.7 Hz, 2H), 5.93 (d, J=7.1 Hz, 1H).

Workup

  1. temperaturecooled
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto afford

Sources & evidence

ORD record
ord-a75ae7fe4b1a4ea99bd6b3649001a6a4
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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