1,2-Dichloroethane → HCID 22054038, compound

HRID 1830173Notes

Reaction equation

HRID 1830173 reaction equation
[N:1]1([C:7](=[O:24])[CH2:8][CH:9]([CH2:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:15])[C:10]([OH:12])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O[C:26]([C:28](F)(F)F)=O.[NH2:32][C:33]([CH3:46])(C)[C:34]([C:36]1[O:37][C:38]2C([N:44]=1)=NC=[CH:42][CH:43]=2)=[O:35].C1C=CC2N(O)N=[N:53]C=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[CH2:43]([C:38]1[O:37][C:36]([CH:34]([OH:35])[CH:33]([NH:32][C:10](=[O:12])[CH:9]([CH2:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:15])[CH2:8][C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[O:24])[CH2:46][CH2:26][CH3:28])=[N:44][N:53]=1)[CH3:42]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220539874-Morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyric acidHCID 86611135HCID 86611135, compound

Product 1

HCID 22054038HCID 22054038, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyric acid (142 mg, 0.4 mmol), 2-amino-2-methyl-1-oxazolo[4,5-b]pyridin-2-yl-propan-1-one TFA salt (165 mg), prepared as in reference 14, and HOBt (73 mg, 0.45 mmol) in MeCl2 (5 ml) was added EDC (115 mg, 0.6 mmol) and N-methylmorpholine (0.25 ml) at room temperature. After stirring for 14 hours, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, dried with MgSO4 and concentrated. The residue was purified by silica gel column chromatography to yield 92 mg of N-{1-[(5-Ethyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-butyl}-4-morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyramide.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-11112933b57f454bbb6b4827faa26123
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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