3-Chloro-1-propanol → HCID 18408622, compound

HRID 992980Notes

Reaction equation

HRID 992980 reaction equation
I[C:2]1[N:6]([CH3:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][N:3]=1.CN1C(C2C=CC=CC=2)=NN=C1.[C:26]([C:30]1[N:35]=[C:34]([N:36]2[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][CH2:44][OH:45])[CH2:38][CH2:37]2)[CH:33]=[C:32]([C:46]([F:49])([F:48])[F:47])[N:31]=1)([CH3:29])([CH3:28])[CH3:27].ClCCCO.[H-].[Na+]>CN(C=O)C>[C:26]([C:30]1[N:35]=[C:34]([N:36]2[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][CH2:44][O:45][C:2]3[N:6]([CH3:7])[C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)=[N:4][N:3]=3)[CH2:38][CH2:37]2)[CH:33]=[C:32]([C:46]([F:48])([F:49])[F:47])[N:31]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 5

HCID 123133-Chloro-1-propanolHCID 24758Sodium hydrideHCID 11499260HCID 11499260, compoundHCID 18408602HCID 18408602, compoundHCID 18408633HCID 18408633, compound

Product 1

HCID 18408622HCID 18408622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

855 mg (3mmol) of 3-iodo-4-methyl-5-phenyl-1,2,4-(4H)-triazole (prepared by iodinating 4-methyl-5-phenyl-1,2,4-(4H)-triazole by a method similar to Izv. Akad. Nauk SSSR, Ser. Khim (1975), 616-619), were stirred, at 60° C. for 6 h, with 1.04 g (3 mmol) of 2-t-butyl-4-[4-(3-hydroxypropyl)piperazin-1-yl]-6-trifluoromethyl pyrimidine (prepared, by a method similar to Example 1, A.3, by reacting the product obtained as described in Example 1, A.2 with 3-chloropropanol) and sodium hydride in DMF. For the working-up, ice water was added to the mixture and the whole was extracted several times with methyl t-butyl ether. The residue which was obtained after drying with sodium sulfate and removing the solvent was purified by column chromatography (silica gel, methylene chloride/methanol). Yield, 140 mg (9% of theory) of oil.

Workup

  1. customprepared, by a method similar to Example 1, A.3
  2. customobtained
  3. extractionthe whole was extracted several times with methyl t-butyl ether
  4. customThe residue which was obtained
  5. dry with materialafter drying with sodium sulfate
  6. customremoving the solvent
  7. customwas purified by column chromatography (silica gel, methylene chloride/methanol)
  8. customYield

Sources & evidence

ORD record
ord-122c73f9ece747fc9e17ff11ce286c89
Source dataset
uspto-grants-2002_10
Patent number
US06472392B1

Reaction notes

Loading…