Potassium Carbonate → (S)-2-Acetylamino-oxazole-4-carboxylic acid (1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-amide

HRID 1617325Notes

Reaction equation

HRID 1617325 reaction equation
[C:1]([NH:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([OH:12])=O)[N:9]=1)(=[O:3])[CH3:2].Cl.[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([C@@H:35]([NH2:37])[CH3:36])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)[CH3:15].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:14]([O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]2[CH2:24][CH2:25][N:26]([C:29]3[CH:30]=[CH:31][C:32]([C@@H:35]([NH:37][C:10]([C:8]4[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[O:6][CH:7]=4)=[O:12])[CH3:36])=[CH:33][CH:34]=3)[CH2:27][CH2:28]2)=[CH:21][CH:22]=1)[CH3:15]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 840118932-Acetamidooxazole-4-carboxylic acidHCID 86688559(S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride

Product 1

HCID 71617629(S)-2-Acetylamino-oxazole-4-carboxylic acid (1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2.0 mg (0.012 mmol) 2-acetylamino-oxazole-4-carboxylic acid, 3.6 mg (S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride (XII.1) and 3.54 (0.02 mmol) DIPEA in 0.27 mL DMF are added 3.9 mg (0.012 mmol) TBTU. The mixture is shaken at rt for 12 h. 25 μl K2CO3 solution (3 M) is added, the mixture is filtered through basic alumina, washed with DMF/MeOH (9:1) and concentrated to yield the desired product.

Workup

  1. filtrationthe mixture is filtered through basic alumina
  2. washwashed with DMF/MeOH (9:1)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ba72a864b84b43a4998dcd36e9970d72
Source dataset
uspto-grants-2014_07
Patent number
US08765959B2

Reaction notes

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