Water → HCID 22709729, compound

HRID 352917Notes

Reaction equation

HRID 352917 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:38]=[CH:37][C:14]([C:15]([N:17]3[CH2:22][CH2:21][N:20]([S:23]([C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[C:31]([Cl:36])[CH:32]=5)[CH:27]=4)(=[O:25])=[O:24])[CH2:19][CH2:18]3)=[O:16])=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[ClH:36].[NH2:1][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:38]=[CH:37][C:14]([C:15]([N:17]3[CH2:22][CH2:21][N:20]([S:23]([C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[C:31]([Cl:36])[CH:32]=5)[CH:27]=4)(=[O:24])=[O:25])[CH2:19][CH2:18]3)=[O:16])=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 22711098HCID 22711098, compound

Product 1

HCID 22709729HCID 22709729, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, 1-[4-(2-azidomethylpyridin-4-yl)benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine (159 mg) was dissolved in tetrahydrofuran (5 ml), followed by the addition of water (0.5 ml) and triphenylphosphine (114 mg). The resulting mixture was stirred for 18 hours. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (10% methanol—dichloromethane), followed by dissolution in dichloromethane. To the resulting solution, 1N hydrochloric acid in ethanol and water were added. The resulting mixture was then concentrated. The crystals were collected by filtration and washed with ethyl acetate, whereby the title compound (53 mg, 30%) was obtained.

Workup

  1. customThe residue obtained
  2. distillationby distilling off the solvent under reduced pressure
  3. customwas purified by chromatography on a silica gel column (10% methanol—dichloromethane)
  4. dissolutionfollowed by dissolution in dichloromethane
  5. additionTo the resulting solution, 1N hydrochloric acid in ethanol and water were added
  6. concentrationThe resulting mixture was then concentrated
  7. filtrationThe crystals were collected by filtration
  8. washwashed with ethyl acetate, whereby the title compound (53 mg, 30%)
  9. customwas obtained

Sources & evidence

ORD record
ord-17b7246a318e4abaa926e11b788508bc
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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