Triethylamine → HCID 56654398, compound

HRID 1961544Notes

Reaction equation

HRID 1961544 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:28]([F:31])([F:30])[F:29])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4([F:27])[CH2:26][NH:25][CH2:24]4)=[CH:19][CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N(CC)CC)C.[S:39](Cl)([CH3:42])(=[O:41])=[O:40]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:28]([F:31])([F:29])[F:30])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4([F:27])[CH2:26][N:25]([S:39]([CH3:42])(=[O:41])=[O:40])[CH2:24]4)=[CH:19][CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86661739HCID 86661739, compound

Product 1

HCID 56654398HCID 56654398, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3-chloro-5-(trifluoromethyl)phenyl)-3-(4-(3-fluoroazetidin-3-yl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (Preparation 22, 95 mg, 0.2 mmol) in CH2Cl2 (5 mL) was added triethylamine (0.15 mL, 1.1 mmol) and DMAP (5 mg, 0.04 mmol). Contents were stirred for 30 minutes at which time mesyl chloride (25 mg, 0.2 mmol) was added and the reaction was stirred for 18 hours at room temperature. Next, the reaction was concentrated to ˜3 mL under nitrogen purge and injected directly onto a 24 g Redi-Sep column. The crude material was chromatographed eluting from 100% heptane to 30:70 EtOAc:heptane to afford the final product (95 mg, 94%) as a solid. 1HNMR (CDCl3) δ ppm: 7.85 (1H), 7.79-7.77 (3H), 7.72 (1H), 7.64 (2H), 4.50-4.42, (2H), 4.34-4.27 (2H), 4.18 (1H), 3.76 (1H), 3.03 (3H); m/z (Cl) 545 ([M+H]+.

Workup

  1. additionwas added
  2. concentrationNext, the reaction was concentrated to ˜3 mL under nitrogen
  3. custompurge
  4. customThe crude material was chromatographed
  5. washeluting from 100% heptane to 30:70 EtOAc

Sources & evidence

ORD record
ord-d719468a17a9427788f7e6ad751c903f
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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