Dichloromethane → HCID 22480023, compound

HRID 1349692Notes

Reaction equation

HRID 1349692 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[N:22]=[CH:21][N:20](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:19]=4)[CH:16]=3)[N:11](C3CCCCO3)[N:10]=2)=[CH:5][CH:4]=1.C(Cl)Cl.ClC1C=C(C=CC=1)C(OO)=[O:56]>CCOC(C)=O>[NH:19]1[C:18]([C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[C:6]2[CH:7]=[CH:8][C:3]([S:2]([CH3:1])=[O:56])=[CH:4][CH:5]=2)=[N:22][CH:21]=[N:20]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 22479934HCID 22479934, compound

Product 1

HCID 22480023HCID 22480023, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methylthio-1-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}benzene (136 mg, 0.214 mmol), 1.00 mL CH2Cl2, and 3-chloroperoxybenzoic acid (Aldrich, 77% purity, 48.1 mg, 0.214 mmol based on 77% purity, 1.00 equiv.) was stirred at room temperature for 30 minutes. The reaction was diluted with EtOAc, washed with 2×sat. aq. NaHCO3, dried (Na2SO4), filtered, and concentrated. The crude concentrate was heated in 5.00 mL of MeOH and 5.00 mL of 6.0 N aq. HCl at 65° C. for 17.5 h. The mixture was poured onto 6.0 N aq. NaOH and extracted with 2×EtOAc. The aqueous layer was neutralized to pH=6.0 with 6.0 N aq. HCl, and extracted with 2×EtOAc. The combined organics were dried (Na2SO4), filtered, and concentrated. Purification by prep HPLC afforded the title compound (7.2 mg, 10.4% yield): 1H NMR (CDCl3/CD3OD) δ 8.78 (s, 1H), 8.45–7.98 (m, 4H), 7.86 (d, 2H), 7.72 (d, 1H), 2.89 (s, 3H); ES-MS (m/z) 324 [M+1]+.

Workup

  1. washwashed with 2×
  2. dry with materialaq. NaHCO3, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationThe crude concentrate
  6. temperaturewas heated in 5.00 mL of MeOH
  7. wait5.00 mL of 6.0 N aq. HCl at 65° C. for 17.5 h
  8. additionThe mixture was poured onto 6.0 N aq. NaOH
  9. extractionextracted with 2×EtOAc
  10. extractionextracted with 2×EtOAc
  11. dry with materialThe combined organics were dried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customPurification by prep HPLC

Sources & evidence

ORD record
ord-cefce23f2e8b41ccaec85a376f48820e
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…