Hydrazine → 4-{5-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(3-fluoroazetidin-1-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzohydrazide

HRID 531283Notes

Reaction equation

HRID 531283 reaction equation
[F:1][C:2]([F:53])([F:52])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([C:34]5[C:43]([CH3:44])=[CH:42][C:37]([C:38]([O:40]C)=O)=[CH:36][C:35]=5[CH3:45])[CH:29]=[N:30][C:31]=4[O:32][CH3:33])=[CH:24][N:23]=[C:22]([N:46]4[CH2:49][CH:48]([F:50])[CH2:47]4)[N:21]=3)[C@H:14]2[CH3:51])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH2:54][NH2:55]>C(O)C>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([C:34]5[C:35]([CH3:45])=[CH:36][C:37]([C:38]([NH:54][NH2:55])=[O:40])=[CH:42][C:43]=5[CH3:44])[CH:29]=[N:30][C:31]=4[O:32][CH3:33])=[CH:24][N:23]=[C:22]([N:46]4[CH2:49][CH:48]([F:50])[CH2:47]4)[N:21]=3)[C@H:14]2[CH3:51])[CH:4]=[C:3]([C:2]([F:52])([F:1])[F:53])[CH:8]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 90009151HCID 90009151, compound

Product 1

HCID 900090934-{5-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(3-fluoroazetidin-1-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(3-fluoroazetidin-1-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzoate (EXAMPLE 32 Step A, 0.091 g, 0.122 mmol) was dissolved in ethanol (0.80 mL). Added hydrazine (0.115 mL, 3.65 mmol) and stirred at 85° C. in a screw cap vial (with a pressure relief cap) under a nitrogen blanket. The reaction was monitored by LCMS. Once complete the reaction was cooled to room temperature. The solvent was removed by rotary evaporation and the crude isolate was partitioned between ethyl acetate and water. Washed the organic twice more with water, then once with brine, dried over sodium sulfate, filtered and evaporated to give an off-white foam as the product. The compound was used without further purification. 1H NMR (CDCl3, 500 MHz): δ 8.15 (s, 1H), 8.00 (d, 1H), 7.88 (s, 1H), 7.74 (s, 2H), 7.51 (d, 2H), 7.43 (s, 1H), 7.27 (d, 1H), 5.70 (d, 1H), 5.51 (m, 0.5H), 5.40 (m, 0.5H), 4.69 (d, 1H), 4.45 (m, 3H), 4.29 (m, 2H), 3.99 (m, s, 4H), 2.14 (s, 3H), 2.13 (s, 3H), 1.65 (br, 2H), 0.74 (d, 3H).

Workup

  1. customcap vial (with a pressure relief
  2. customcap) under a nitrogen blanket
  3. customThe solvent was removed by rotary evaporation
  4. customthe crude isolate
  5. customwas partitioned between ethyl acetate and water
  6. washWashed the organic twice more with water
  7. dry with materialonce with brine, dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give an off-white foam as the product
  11. customThe compound was used without further purification

Sources & evidence

ORD record
ord-12c516e455d44adea98afd55abdd2ae3
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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