Hydrochloric Acid → HCID 22245074, compound

HRID 1979271Notes

Reaction equation

HRID 1979271 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[CH:16]2.N1C=CC=CC=1.O.[OH-].[Li+].CO.Cl>O1CCCC1>[CH2:5]([O:4][C:2]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[CH:16]2)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1049PyridineHCID 10387Benzyl chloroformateHCID 880121H-Indazol-5-amineHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 22245074HCID 22245074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzyl chloroformate (9.9 ml, ca. 66 mmol) in tetrahydrofuran (66 ml) was added dropwise with stirring to 5-aminoindazole (4.44 g, 33 mmol) in tetrahydrofuran (150 ml) and pyridine (12.0 ml, 150 mmol) at −5° C. The mixture was allowed to warm to room temperature, stirred for 4 h, and concentrated under vacuum. Ethyl acetate (100 ml) and water (150 ml) were added, and the aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with 0.3 N aq. HCl (2×100 ml), water, brine, and dried (MgSO4). Solvent was removed under vacuum to afford the crude product as a mixture of two regioisomers. MS (m/z): 402.1 [M+H]+. 0.3 M lithium hydroxide monohydrate in methanol (250 ml, ca. 75 mmol) was added. The mixture was stirred at room temperature for 45 min and then carefully acidified with 6 N aq. HCl until the pH of the solution was 2. The resulting product was filtered off, washed with water and dried under vacuum to afford the desired compound. Rt 4.2 min. MS (m/z): 268.1 [M+H]+. 1H NMR.

Workup

  1. concentrationconcentrated under vacuum
  2. additionEthyl acetate (100 ml) and water (150 ml) were added
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×100 ml)
  4. washThe combined organic layers were washed with 0.3 N aq. HCl (2×100 ml), water, brine
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed under vacuum
  7. customto afford the crude product
  8. additionas a mixture of two regioisomers
  9. stirringThe mixture was stirred at room temperature for 45 min
  10. filtrationThe resulting product was filtered off
  11. washwashed with water
  12. customdried under vacuum

Sources & evidence

ORD record
ord-b70d963058b94be29440da6131920893
Source dataset
uspto-grants-2001_05
Patent number
US06239152B1

Reaction notes

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