1,2-Dichloroethane → HCID 59252361, compound

HRID 1947676Notes

Reaction equation

HRID 1947676 reaction equation
[CH3:1][CH:2]([CH3:9])[CH2:3][C:4](=[O:8])[C:5]([OH:7])=O.O.ON1C2C=CC=CC=2N=N1.C(Cl)CCl.[CH3:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH2:40][CH2:39][CH:38]([CH:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)[CH2:37][CH2:36]2)=[CH:31][CH:30]=1)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:9][CH:2]([CH3:1])[CH2:3][C:4](=[O:8])[C:5]([N:44]1[CH2:43][CH2:42][CH:41]([CH:38]2[CH2:37][CH2:36][N:35]([C:32]3[CH:31]=[CH:30][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:34][CH:33]=3)[CH2:40][CH2:39]2)[CH2:46][CH2:45]1)=[O:7]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 704-Methyl-2-oxovaleric acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 591788671[4-(Methylsulfonyl)phenyl]-4,4'-bipiperidine

Product 1

HCID 59252361HCID 59252361, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methyl-2-oxovaleric acid (8.07 mg; 0.062 mmol) was treated sequentially with 1-hydroxybenzotriazole hydrate (11.4 mg; 0.0741 mmol), EDC (14.3 mg; 0.074 mmol) and 1 1-[4-(methylsulfonyl)phenyl]-4,4′-bipiperidine (20.0.0 mg; 0.062 mmol) and stirred at ambient temperature for 18 h. The reaction was diluted with CH2Cl2(10 mL) and washed with water (15 mL). The organic phase was then dried over Na2SO4, filtered and concentrated in. vac to a residue. The crude product was purified by preparative HPLC reserve phase and eluted with acetonitrile/water+0.1% TFA. The title compound was isolated.

Workup

  1. washwashed with water (15 mL)
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in
  5. customThe crude product was purified by preparative HPLC reserve phase
  6. washeluted with acetonitrile/water+0.1% TFA

Sources & evidence

ORD record
ord-d4502b322ebb483a8f894d6a6d05d378
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

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