Bromine → (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)-3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one

HRID 539134Notes

Reaction equation

HRID 539134 reaction equation
[F:1][C:2]1[CH:13]=[C:12]([C:14]2[CH:15]=[N:16][N:17]3[CH:22]=[CH:21][C:20]([N:23]4[C@@H:27]([C:28]5[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=5)[CH2:26][O:25][C:24]4=[O:35])=[N:19][C:18]=23)[CH:11]=[CH:10][C:3]=1/[CH:4]=[N:5]/[NH:6][C:7]([NH2:9])=[O:8].C([O-])(=O)C.[Na+].BrBr>C(O)(=O)C>[NH2:9][C:7]1[O:8][C:4]([C:3]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[N:16][N:17]4[CH:22]=[CH:21][C:20]([N:23]5[C@@H:27]([C:28]6[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=6)[CH2:26][O:25][C:24]5=[O:35])=[N:19][C:18]=34)=[CH:13][C:2]=2[F:1])=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 87243681[(E)-[2-fluoro-4-[5-[(4S)-4-(5-fluoro-2-pyridinyl)-2-oxo-1,3-oxazolidin-3-yl]pyrazolo[1,5-a]pyrimidin-3-yl]phenyl]methylideneamino]urea

Product 1

HCID 67034781(S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)-3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-oneYield 31%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of (S,E)-2-(2-fluoro-4-(5-(4-(5-fluoropyridin-2-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzylidene)hydrazinecarboxamide (26 mg, 0.054 mmol) in acetic acid (0.6 mL) was added sodium acetate (44 mg, 0.54 mmol). After complete dissolution of the salt, a dilute solution of Br2 (2.7 μL, 0.054 mmol) in acetic acid was slowly added dropwise in portions. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was applied directly on a preparative TLC plate. Acetic acid was removed under a stream of air, and the preparative TLC plate was developed with 10% MeOH in DCM to afford (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)-3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (7.9 mg, 31% yield) as a yellow solid. MS (APCI+) m/z 477 [M+H]+.

Workup

  1. dissolutionAfter complete dissolution of the salt
  2. customAcetic acid was removed under a stream of air

Sources & evidence

ORD record
ord-2cd6da3776a54bf0a3b67f522f7a6101
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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