4-Toluenesulfonyl chloride → HCID 11257184, compound

HRID 1661183Notes

Reaction equation

HRID 1661183 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([NH:16][NH:17][C:18](=O)[C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[O:15])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C>O1CCCC1>[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[O:15][C:18]([C:19]4[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=4)=[N:17][N:16]=3)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine2×HCID 51508031HCID 51508031, compound

Product 1

HCID 11257184HCID 11257184, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-fluoro-benzoic acid N′-[(S)-1-(4-fluoro-benzoyl)-piperidine-3-carbonyl]-hydrazide (100 mg, 0.26 mmol), 4-toluenesulphonyl chloride (60 mg, 0.31 mmol), solid supported 2-tert-Butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diaza-phosphorine (PS-BEMP, ex Fluka, 586 mg, 1.3 mmol, loading 2.2 mmol/g) in dry tetrahydrofuran (6 mL) was irradiated by microwaves under the following conditions: MW cycle: t=1 min, P=100 W, cooling time=2 min. After 5 MW cycles, the resin was filtered off and washed repeatedly with dichloromethane. The solvent was evaporated under reduced pressure to give a crude solid that was purified by flash chromatography (silica gel, eluent: hexane/ethyl acetate 1:1). The title compound was obtained as a white solid (82 mg).

Workup

  1. customwas irradiated by microwaves under the following conditions
  2. temperatureMW cycle: t=1 min, P=100 W, cooling time=2 min
  3. filtrationAfter 5 MW cycles, the resin was filtered off
  4. washwashed repeatedly with dichloromethane
  5. customThe solvent was evaporated under reduced pressure
  6. customto give a crude solid that
  7. customwas purified by flash chromatography (silica gel, eluent: hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-b6f0f36e59204afd94489b6cb691cd6e
Source dataset
uspto-grants-2011_10
Patent number
US08030331B2

Reaction notes

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