1,4-Dioxane → HCID 71230899, compound

HRID 2172691Notes

Reaction equation

HRID 2172691 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[O:25][N:24]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9]1)=O)(C)(C)C.O1CCOCC1>Cl>[NH:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[O:25][N:24]=3)=[CH:19][CH:18]=2)(=[O:15])=[O:16])[CH2:9]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 86719162HCID 86719162, compound

Product 1

HCID 71230899HCID 71230899, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(R)—N-(pyrrolidin-3-yl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzenesulfonamide was synthesized as (R)-3-[4-(5-trifluoromethyl-[1,2,4]oxadiazol-3-yl)-benzenesulfonylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester and the Boc protecting group removed as follows: (277 mg, 0.612 mmol) of the crude coupling product was dissolved in HCl in Dioxane (1531 μL, 6.12 mmol) and stirred for 12 hr. It was concentrated to dryness to receive a brown solid. The crude product was subjected to purification by reverse phase prep-HPLC (gradient elution, water/MeCN both containing 0.1% TFA). Fractions containing the desired compound were combined and freeze-dried. The resulting mixture was dissolved in a mix of AcCN/water. They were load in a PL-HCO3 MP cartridge (from StratoSpheres™ SPE) and eluted with ACN. The eluate was freeze-dried to yield the final compound.

Workup

  1. customthe Boc protecting group removed
  2. concentrationIt was concentrated to dryness
  3. customThe crude product was subjected to purification by reverse phase prep-HPLC (
  4. washgradient elution, water/MeCN both containing 0.1% TFA)
  5. additionFractions containing the desired compound
  6. customfreeze-dried
  7. dissolutionThe resulting mixture was dissolved in
  8. additiona mix of AcCN/water
  9. washeluted with ACN
  10. customThe eluate was freeze-dried

Sources & evidence

ORD record
ord-56906fe5abe444e1ba9bfa785aaaf669
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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