1,2-Dichloroethane → N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-2-benzylsulfonyl-methyl-butyramide

HRID 1830185Notes

Reaction equation

HRID 1830185 reaction equation
O=C(N1CCCCC1)C[CH:4]([CH2:8][S:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:11])=[O:10])[C:5]([OH:7])=O.[OH:25][C:26](C(F)(F)F)=O.[NH2:32][CH:33]([CH2:47][CH3:48])[CH:34]([C:36]1[O:37][C:38]([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)=[N:39][N:40]=1)[OH:35].[CH:49]1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C[N:64]1[CH2:69][CH2:68][O:67][CH2:66][CH2:65]1>C(Cl)Cl>[OH:35][CH:34]([C:36]1[O:37][C:38]([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)=[N:39][N:40]=1)[CH:33]([NH:32][C:26](=[O:25])[C:8]([CH3:49])([S:9]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:10])=[O:11])[CH2:4][C:5]([N:64]1[CH2:69][CH2:68][O:67][CH2:66][CH2:65]1)=[O:7])[CH2:47][CH3:48]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220539604-Oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyric acidHCID 866111392-amino-1-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol TFA salt

Product 1

HCID 22054030N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-2-benzylsulfonyl-methyl-butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stiffed mixture of 4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyric acid (105.9 mg, 0.3 mmol), 2-amino-1-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol TFA salt (105 mg), prepared as in reference 18, and HOBt (55 mg, 0.36 mmol) in MeCl2 (5 ml), was added EDC (86.4 mg, 0.45 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 to yield 176 mg of N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-2-benzylsulfonyl-methyl-butyramide; MS: 570.2(M−1), 572(M+1).

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

Sources & evidence

ORD record
ord-e5ca2c19171c425c9259126ac701181a
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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