Water → HCID 11656056, compound

HRID 1713730Notes

Reaction equation

HRID 1713730 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:21][CH:22]=2)=[O:15])=[N:11][N:10]=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CN(C=O)C.N1C=CC=CC=1>[C:29]([N:26]1[CH2:27][CH2:28][N:23]([C:20]2[N:19]=[CH:18][C:17]([NH:16][C:14]([C:12]3[O:13][C:9]([NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[N:10][N:11]=3)=[O:15])=[CH:22][CH:21]=2)[CH2:24][CH2:25]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 59464054HCID 59464054, compound2×

Product 1

HCID 11656056HCID 11656056, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

5-[(2-Fluorophenyl)amino]-N-(6-piperazin-1-ylpyridin-3-yl)-1,3,4-oxadiazole-2-carboxamide (intermediate 41, 150 mg, 0.39 mmol), was stirred in DMF (4 mL) and pyridine (1 mL). Benzoyl chloride (60 mg, 0.43 mmol) was added and the reaction stirred for 18 h. Water (20 mL) was added and the reaction mixture thoroughly mixed. The resulting precipitate was filtered, washed with water (2×10 mL) then ether (2×10 mL) and dried in vacuo to give the title compound (130 mg) as a pale purple solid:

Workup

  1. additionthe reaction mixture thoroughly mixed
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water (2×10 mL)
  4. dry with materialether (2×10 mL) and dried in vacuo

Sources & evidence

ORD record
ord-9a7bd9e529f147feae8d0f1c8fd98343
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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