Phosphorus pentachloride → HCID 178526362, compound

HRID 1663497Notes

Reaction equation

HRID 1663497 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2C(=O)[O:12][N:11]=[C:10]2[C:15]2[C:16]([NH:20][C:21]([C:23]3[NH:27][N:26]=[N:25][N:24]=3)=O)=[N:17][O:18][N:19]=2)[CH:5]=[CH:6][C:7]=1[F:8].P(Cl)(Cl)(Cl)(Cl)Cl.C([BH3-])#N.[Na+]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:15]2[C:16]([NH:20][CH2:21][C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[N:17][O:18][N:19]=2)=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 5003444Sodium cyanoborohydrideHCID 178522737HCID 178522737, compound

Product 1

HCID 178526362HCID 178526362, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-1H-tetrazole-5-carboxamide (12 mg, 27 μmol) in pyridine (0.3 mL) was treated with phosphorus pentachloride (13 mg, 60 μmol) at 25° C. The reaction mixture was stirred at 0° C. for 2 h, concentrated, rediluted with toluene and concentrated to a residue. This material was diluted with ethanol (1 mL), treated with sodium cyanoborohydride (5 mg, 82 μmol), and stirred for 2 h. The reaction mixture was concentrated, diluted with ethanol (1 mL), treated with 2.0 M sodium hydroxide in water (0.2 mL), and stirred for 45 min. Purification of the crude reaction mixture by preparative LCMS gave the desired product (2 mg, 19%). LCMS for C11H10BrFN9O2 (M+H)+: m/z=398.0, 400.0.

Workup

  1. concentrationconcentrated
  2. additionrediluted with toluene
  3. concentrationconcentrated to a residue
  4. additionThis material was diluted with ethanol (1 mL)
  5. stirringstirred for 2 h
  6. concentrationThe reaction mixture was concentrated
  7. additiondiluted with ethanol (1 mL)
  8. additiontreated with 2.0 M sodium hydroxide in water (0.2 mL)
  9. stirringstirred for 45 min
  10. customPurification of the crude
  11. customreaction mixture by preparative LCMS

Sources & evidence

ORD record
ord-1060500441b9499e96949d05f4e49008
Source dataset
uspto-grants-2011_10
Patent number
US08034953B2

Reaction notes

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