Hydrazine → HCID 90009156, compound

HRID 531295Notes

Reaction equation

HRID 531295 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[CH:43]=[CH:42][C:37]([C:38]([O:40]C)=O)=[CH:36][C:35]=5[CH3:44])[CH:29]=[N:30][C:31]=4[O:32][CH3:33])=[CH:24][N:23]=[C:22]([N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]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:52][C:2]([F:1])([F:53])[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[CH:43]=[CH:42][C:37]([C:38]([NH:54][NH2:55])=[O:40])=[CH:36][C:35]=5[CH3:44])[CH:29]=[N:30][C:31]=4[O:32][CH3:33])=[CH:24][N:23]=[C:22]([N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)[N:21]=3)[C@H:14]2[CH3:51])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 90009166HCID 90009166, compound

Product 1

HCID 90009156HCID 90009156, compound

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-(morpholin-4-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (EXAMPLE 39 Step A, 0.114 g, 0.153 mmol) was dissolved in ethanol (1.0 mL). Added hydrazine (0.144 mL, 4.59 mmol), and stirred at 85° C. in a screw cap vial (Pressure type) under a nitrogen blanket. Once complete, 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 8.18 (m, 2H), 7.88 (s, 1H), 7.71 (m, 3H), 7.61 (d, 1H), 7.45 (d, 1H), 7.35 (s, 1H), 7.31 (d, 1H), 5.63 (d, 1H), 4.74 (d, 1H), 4.33 (m, 1H), 4.10 (m, 2H), 4.00 (m, s, 4H), 3.86 (m, 4H), 3.80 (m, 4H), 2.37 (s, 3H), 0.72 (d, 3H).

Workup

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

Sources & evidence

ORD record
ord-c49b944d167a42029d12c152153b76ad
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

Loading…