HCID 57941341, compound → HCID 57941479, compound

HRID 1437948Notes

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

Conditions

Temperature: 100 °C

Procedure

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and 4-bromomethyl-3-trifluoromethyl-1-trityl-1H-pyrazole (0.23 g, 0.49 mmol) in N,N-dimethylformamide (5 mL) was heated at 100° C. over the weekend. The reaction mixture was evaporated and the residue was purified by flash chromatography, eluting with 3% methanol/dichloromethane, followed by drying under high vacuum to give (4S,7R)-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 (213 mg, 73%).

Workup

customThe reaction mixture was evaporated
customthe residue was purified by flash chromatography
washeluting with 3% methanol/dichloromethane
customby drying under high vacuum

Sources & evidence

ORD record: ord-93cc34f2a7fc4feb8f13dbf3b634bd2f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

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