Hydrazine hydrate (1:1) → HCID 178440959, compound

HRID 1879634Notes

Reaction equation

HRID 1879634 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:41])[C:5](F)=[C:6]([C:8](=O)[CH:9]([CH:17]([C:21]2[CH:38]=[CH:37][C:24]([C:25]([NH:27][CH2:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])=[O:26])=[CH:23][CH:22]=2)[CH2:18][CH2:19][CH3:20])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:7]=1.O.[NH2:43][NH2:44]>CS(C)=O>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([CH:9]([C:8]2[C:6]3[C:5](=[C:4]([F:41])[CH:3]=[C:2]([C:3]4[CH:2]=[CH:7][C:6]([CH3:8])=[CH:5][CH:4]=4)[CH:7]=3)[NH:44][N:43]=2)[CH:17]([C:21]2[CH:38]=[CH:37][C:24]([C:25]([NH:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:26])=[CH:23][CH:22]=2)[CH2:18][CH2:19][CH3:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58538064HCID 58538064, compound

Product 1

HCID 178440959HCID 178440959, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the product of Step F (600 mg, 0.925 mmol) in DMSO (10 mL) was added hydrazine hydrate (60 wt %, 2.0 mL, 24 mmol). The mixture was stirred at room temperature until all starting ketone had been consumed by LC-MS analysis. The mixture was diluted with ethyl acetate then washed with saturated NaCl (aq). The organic layer was dried over sodium sulfate, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-50% EtOAc/hexanes to afford the title compound as a solid. LC2 1.40 min. (M+H)+644.

Workup

  1. customhad been consumed by LC-MS analysis
  2. additionThe mixture was diluted with ethyl acetate
  3. washthen washed with saturated NaCl (aq)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel chromatography
  8. washeluting with 0-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-5d3854bca65d4436a1ca9ec03b4f6c9f
Source dataset
uspto-grants-2012_11
Patent number
US08318667B2

Reaction notes

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