HCID 57941342, compound → HCID 57941494, compound

HRID 1438082Notes

Reaction equation

HRID 1438082 reaction equation
[CH3:1][N:2]1[C:10]2[C@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.Br[CH2:17][C:18]1[C:19]([C:42]([F:45])([F:44])[F:43])=[N:20][N:21]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=1>CN(C)C=O>[CH3:1][N:2]1[C:10]2[C@:9]3([CH3:14])[C:11]([CH3:12])([CH3:13])[C@@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[N:3]1[CH2:17][C:18]1[C:19]([C:42]([F:45])([F:43])[F:44])=[N:20][N:21]([C:23]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=1

Participants

4

Reactant 2

HCID 57941342HCID 57941342, compound2×HCID 57941503HCID 57941503, compound2×

Product 1

HCID 57941494HCID 57941494, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4R,7S)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 48; 250 mg, 1.2 mmol) and 4-bromomethyl-3-trifluoromethyl-1-trityl-1H-pyrazole (Intermediate 2; 580 mg, 1.2 mmol) in dimethylformamide (12 mL) was heated at 100° C. for 4.5 h. The solvent was evaporated and the residue was purified on a Biotage 40S chromatography system, eluting with 0-3% methanol/dichloromethane. Fractions homogeneous for the product were concentrated and the residue held under high vacuum to give (4R,7S)-1,7,8,8-tetramethyl-2-(3-trifluoromethyl-1-trityl-1H-pyrazol-4-ylmethyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (420 mg, 58%) as a viscous golden orange oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on a Biotage 40S chromatography system
  3. washeluting with 0-3% methanol/dichloromethane
  4. concentrationFractions homogeneous for the product were concentrated

Sources & evidence

ORD record
ord-a669e4f31bde4502b88e6311cc389794
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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