Hydrochloric Acid → 1,7,8,9-Tetrahydro-pyrano[2,3-g]indazol-8-ol

HRID 1815941Notes

Reaction equation

HRID 1815941 reaction equation
C(NC([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:19][C:20](=O)C)[C:13]=2[CH2:15][CH:16]2C[O:17]2)[CH:8]=[N:7]1)=O)C.C(=O)([O-])[O-].[K+].[K+].O.Cl>CO>[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]3[O:19][CH2:20][CH:16]([OH:17])[CH2:15][C:13]3=2)[CH:8]=[N:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 86759647Acetic acid 1-ethylcarbamoyl-7-oxiranylmethyl-1H-indazol-6-yl ester

Product 1

HCID 224965871,7,8,9-Tetrahydro-pyrano[2,3-g]indazol-8-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Step E (1.44 g, 4.75 mmol) in methanol (100 mL) was added saturated aqueous potassium carbonate (10 mL) and the mixture stirred for 18 h at ambient temperature. Water (200 mL) was added to the reaction mixture and the pH adjusted to 7 with conc HCl followed by extraction ethyl acetate (5×100 mL). The combined extracts were dried (MgSO4) and evaporated to tan solid (0.84 g, 93%): 1H NMR (DMSO-d6) δ 12.77 (s, 1H), 7.94 (s, 1H), 7.49 (d, J=6.0 Hz, 1H), 6.66 (d, J=6.0 Hz, 1H), 5.02 (t, J=6.0 Hz, 1H), 4.85-4.95 (m, 1H), 3.62 (m, 2H), 2.9-3.4 (m, 2H); LC/MS (+APCI) m/z 191 (M+H).

Workup

  1. extractionfollowed by extraction ethyl acetate (5×100 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated to tan solid (0.84 g, 93%)

Sources & evidence

ORD record
ord-f78a7567f263469e87f75b3406eaa021
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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