Water → Talarozole

HRID 1271321Notes

Reaction equation

HRID 1271321 reaction equation
[CH2:1]([CH:3]([CH2:19][CH3:20])[CH:4]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[S:13])=[CH:7][CH:6]=1)[CH3:2].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1S.O>C1COCC1>[CH2:19]([CH:3]([CH2:1][CH3:2])[CH:4]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[S:13][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=2)=[CH:9][CH:10]=1)[N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 87132-AminothiophenolHCID 22603037HCID 22603037, compound

Product 1

HCID 9799888TalarozoleYield 49.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (19b) (0.1665 mol) and 2-aminobenzenethiol (0.2 mol) in THF (500 ml) was stirred and refluxed overnight. The mixture was cooled, poured out into water, extracted with CH2Cl2 and decanted. The organic layer was dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1. The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-butanone/diethyl ether. The precipitate was filtered off and dried, yielding 31.2 g (49.6%) of (±)-N-[4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl]-2-benzothiazolamine (comp. 25).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe mixture was cooled
  3. extractionextracted with CH2Cl2
  4. customdecanted
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from 2-butanone/diethyl ether
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-45cc5afe63b24b30b304f3f462e80de4
Source dataset
uspto-grants-2007_04
Patent number
US07205312B2

Reaction notes

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