Sodium Bicarbonate → HCID 86649764, compound

HRID 1880250Notes

Reaction equation

HRID 1880250 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([Br:28])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)=[CH:5][C:4]=1[Cl:29].[CH3:30][S:31]([CH2:34][C:35](O)=[O:36])(=[O:33])=[O:32].Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>ClCCl.C(Cl)(Cl)Cl>[Br:28][C:20]1[CH:19]=[C:18]([C:12]2([C:14]([F:15])([F:16])[F:17])[O:11][N:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][NH:1][C:35](=[O:36])[CH2:34][S:31]([CH3:30])(=[O:33])=[O:32])=[C:4]([Cl:29])[CH:5]=3)[CH2:13]2)[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37328412-Methanesulfonylacetic acidHCID 86649765HCID 86649765, compound

Product 1

HCID 86649764HCID 86649764, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.15 g of 3-(4-aminomethyl-3-chlorophenyl)-5-[3-bromo-5-(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole and 0.083 g of (methylsulfonyl)acetic acid in 3 mL of dichloromethane, 0.11 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added and the resultant mixture was stirred at room temperature for 15 hours. After the completion of the reaction, the reaction mixture was diluted with 3 mL of chloroform, and then 3 mL of a saturated sodium hydrogen carbonate aqueous solution was added to the diluted reaction mixture, followed by separating off the organic phase. The separated organic phase was dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order. From the resultant organic phase, the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate to obtain 0.14 g of the objective substance as a white crystal.

Workup

  1. customAfter the completion of the reaction
  2. customby separating off the organic phase
  3. dry with materialdried over saturated saline and anhydrous magnesium sulfate in this order
  4. distillationFrom the resultant organic phase, the solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography
  6. washeluting with ethyl acetate
  7. customto obtain 0.14 g of the objective substance as a white crystal

Sources & evidence

ORD record
ord-cc51911c26d34a1abd06db81e778285b
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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