Hydrochloric Acid → HCID 178465658, compound

HRID 539076Notes

Reaction equation

HRID 539076 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:4][CH:3]=1.[CH2:33]([N:35](CC)CC)[CH3:34].Cl.C(=N)(OCC)C.Cl>O.C1COCC1.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH:30][C:33](=[NH:35])[CH3:34])=[O:28])=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 67035490(S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide

Product 1

HCID 178465658HCID 178465658, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a stirred suspension of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (0.062 g, 0.14 mmol) in 2:1 THF-DMF (1.5 mL) was added triethylamine (0.026 mL, 0.19 mmol), followed by ethyl acetimidate hydrochloride (0.021 g, 0.17 mmol) at 0° C. The mixture was allowed to warm up to ambient temperature and stirring continued at 60° C. for 5 hours. The mixture was poured into water, neutralized with 1N HCl, extracted with EtOAc, dried (phase separator silicone treated filter paper) and concentrated to give (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-N′-(1-iminoethyl)benzohydrazide (0.049 g, 72% yield) as a yellow oil.

Workup

  1. extractionextracted with EtOAc
  2. customdried
  3. addition(phase separator silicone treated filter paper)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c9673b8324747f68f3f77cfb3c15f6d
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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