Triethylamine → HCID 86669918, compound

HRID 1506471Notes

Reaction equation

HRID 1506471 reaction equation
[CH3:1][N:2]1[C:11]2[CH:10]=[C:9]([CH:12]=C)[CH:8]=[CH:7][C:6]=2[C:5]2=[N:14][O:15][C:16]([C:17]3[O:21][N:20]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:18]=3[C:28]([F:31])([F:30])[F:29])=[C:4]2[CH2:3]1.[O:32]=[O+][O-].C(N(CC)CC)C>ClCCl>[CH3:1][N:2]1[C:11]2[CH:10]=[C:9]([CH:12]=[O:32])[CH:8]=[CH:7][C:6]=2[C:5]2=[N:14][O:15][C:16]([C:17]3[O:21][N:20]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:18]=3[C:28]([F:31])([F:30])[F:29])=[C:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24823Ozone2×HCID 67168124HCID 67168124, compound

Product 1

HCID 86669918HCID 86669918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methyl-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydroisoxazolo[4,3-c]quinoline (Preparation 77F, 0.020 g, 0.047 mmol) in Dichloromethane (5 mL) at −78° C. was passed ozone from an ozone generator until the solution turned a deep blue. The reaction mixture then was purged with oxygen until the blue color disappeared, then with nitrogen for five minutes. The reaction mixture was allowed to warm to room temperature and triethylamine (5.07 μl, 0.036 mmol) was added. The reaction mixture was stirred at room temperature for fifteen minutes, and then concentrated under vacuum to give 5-methyl-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydroisoxazolo[4,3-c]quinoline-7-carbaldehyde as a tan solid. (0.015 mg, 0.035 mmol, 74%). The product had an HPLC ret. time=3.61 min. (condition B). LC/MS M+1=426.1 min

Workup

  1. customat −78° C.
  2. customThe reaction mixture then was purged with oxygen until the blue color
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-93ee5738eb164f05aaf96b507f7bedac
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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