Hydrochloric Acid → HCID 178423522, compound

HRID 1435085Notes

Reaction equation

HRID 1435085 reaction equation
C(OC(=O)[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=O)[N:27]=[CH:28][N:29](C)C)=[CH:22][C:21]=2[CH3:33])=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.O.[NH2:36]N.[ClH:38]>C(O)(=O)C.CO.O1CCOCC1>[ClH:38].[CH3:33][C:21]1[CH:22]=[C:23]([C:26]2[NH:27][CH:28]=[N:29][N:36]=2)[CH:24]=[CH:25][C:20]=1[C:17]1[CH:16]=[CH:15][C:14]([CH2:13][NH:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 57937836HCID 57937836, compound

Product 1

HCID 178423522HCID 178423522, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

(4′-{[1-Dimethylamino-methylidene]-carbamoyl}-2′-methyl-biphenyl-4-ylmethyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-7a-1: 222 mg, 0.477 mmol) was dissolved in acetic acid (5 ml) and treated with hydrazine monohydrate (0.035 ml, 0.715 mmol). After the reaction mixture was heated at 90° C. for 2 hours, the volatiles were removed and the residue was taken up in ethyl acetate and washed with a saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified using preparative thin layer chromatography eluting with 50% ethyl acetate in hexanes. The product-containing band was isolated and extracted, and the extracts were concentrated under reduced pressure to afford a residue. The residue was dissolved in methanol and treated with 4M HCl in dioxane. After 2 hours, the volatiles were removed under reduced pressure and the resulting solid triturated with hexanes to provide a suspension. The solid was isolated by filtration to afford the title compound (E7-01) as a colorless solid.

Workup

  1. customthe volatiles were removed
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. washeluting with 50% ethyl acetate in hexanes
  8. customThe product-containing band was isolated
  9. extractionextracted
  10. concentrationthe extracts were concentrated under reduced pressure
  11. customto afford a residue
  12. customthe volatiles were removed under reduced pressure
  13. customthe resulting solid triturated with hexanes
  14. customto provide a suspension
  15. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-3999dd1b5544405e9cc033d3aabce60c
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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