Ethyl Acetate → HCID 67301966, compound

HRID 1192469Notes

Reaction equation

HRID 1192469 reaction equation
[N:1]([CH:4]([C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)[CH3:5])=[N+]=[N-].CP(C)C.CCOC(C)=O>O1CCCC1.O>[F:22][C:18]1[CH:17]=[C:16]([C:15]2[C:10]3[N:11]=[C:12]([CH3:14])[S:13][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:4]([NH2:1])[CH3:5])[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 86656161HCID 86656161, compound

Product 1

HCID 67301966HCID 67301966, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-(1-azidoethyl)-4-(3-fluorophenyl)-2-methyl-1,3-benzothiazole (0.088 g, 0.28 mmol) in tetrahydrofuran (0.8 mL) and water (0.203 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (0.338 mL, 0.338 mmol) at room temperature and the mixture was stirred at room temperature for 1 hour. To the mixture was added EtOAc and the mixture was extracted with 1 N HCl two times. The combined extracts were neutralized with solid sodium bicarbonate, and extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue, showing two peaks with the same desired mass, was used directly in next step (74 mg, 91%). LCMS calculated for C16H16FN2S(M+H)+: m/z=287.1; found: 287.1.

Workup

  1. extractionthe mixture was extracted with 1 N HCl two times
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c06dd7f0266e464bb3a3b006077b8f74
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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