Azido(trimethyl)stannane → HCID 178423776, compound

HRID 1269527Notes

Reaction equation

HRID 1269527 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([C:18]3[S:22][C:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[N:20][C:19]=3[CH3:33])=[O:17])[CH2:11]2)=[CH:6][C:3]=1[C:4]#[N:5].C[Sn]([N:38]=[N+:39]=[N-:40])(C)C>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([C:18]3[S:22][C:21]([C:23]4[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=4)=[N:20][C:19]=3[CH3:33])=[O:17])[CH2:11]2)=[CH:6][C:3]=1[C:4]1[NH:40][N:39]=[N:38][N:5]=1

Participants

5

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 68882675(R)-2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzonitrile

Product 1

HCID 178423776HCID 178423776, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

(R)-2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzonitrile (262 mg, 0.56 mmol) was dissolved in toluene (5 mL). Trimethyltin azide (230 mg, 1.12 mmol) was added and the mixture heated at reflux for 24 h. The mixture was diluted with diethyl ether (100 mL) and washed with 0.1 N HCl (100 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 7.5% methanol/chloroform (0.5% ammonium hydroxide modifier). The product fractions were combined and concentrated under reduced pressure. The resultant oil was taken up in 100 mL ethyl acetate and extracted with 0.1 N HCl (100 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 132 mg (46%) of the desired {3-[4-methyl-3-(1H-tetrazol-5-yl)-phenyl]-piperidin-1-yl}-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanone as a clear oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 h
  3. washwashed with 0.1 N HCl (100 mL)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed with 7.5% methanol/chloroform (0.5% ammonium hydroxide modifier)
  8. concentrationconcentrated under reduced pressure
  9. extractionextracted with 0.1 N HCl (100 mL)
  10. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4e0bc90246b414ebe0316bee83d6d35
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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