Hydrochloric Acid → HCID 178434721, compound

HRID 2391103Notes

Reaction equation

HRID 2391103 reaction equation
[C:1]1([C@H:7]([O:9][C:10](=[O:35])[NH:11][C:12]2[C:13]([CH3:34])=[N:14][O:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4([C:32]#[N:33])[CH2:31][CH2:30]4)=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)CCO.Cl.[N-:43]=[N+:44]=[N-:45].[Na+]>COCCOCCOC.C(Cl)Cl.O>[C:1]1([C@H:7]([O:9][C:10](=[O:35])[NH:11][C:12]2[C:13]([CH3:34])=[N:14][O:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[CH:25][C:26]([C:29]4([C:32]5[NH:45][N:44]=[N:43][N:33]=5)[CH2:30][CH2:31]4)=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79022-(Dimethylamino)ethanol2×HCID 33557Sodium AzideHCID 49838936{5-[4'-(1-Cyano-cyclopropyl)-biphenyl-4-yl]-3-methyl-isoxazol-4-yl}-carbamic acid (R)-1-phenyl-ethyl ester

Product 1

HCID 178434721HCID 178434721, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8150DiglymeSolvent

Procedure

{5-[4′-(1-Cyano-cyclopropyl)-biphenyl-4-yl]-3-methyl-isoxazol-4-yl}-carbamic acid (R)-1-phenyl-ethyl ester (0.385 g, 0.83 mmol) and N,N-dimethylethanolamine (0.101 mL, 1.0 mmol) were combined in diglyme (diethylene glycol dimethyl ether; 2 mL). Hydrochloric acid (4M in 1,4-dioxane; 4.2 mL) was added, and the reaction was stirred for 15 minutes. Additional N,N-dimethylethanolamine (0.221 mL, 2.2 mmol) was added, followed by sodium azide (0.098 g, 1.5 mmol), and the reaction was stirred at 120° C. for 24 hours. After cooling to room temperature, the mixture was diluted with CH2Cl2 (20 mL) and H2O (10 mL). The organic layer was dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. stirringthe reaction was stirred at 120° C. for 24 hours
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c5e73e8e354642dca8412819dbb75e7a
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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