Triethylamine → HCID 66823892, compound

HRID 1748100Notes

Reaction equation

HRID 1748100 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)[CH3:2].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]2[C:24]3=[N:25][S:26](=[O:30])(=[O:29])[CH2:27][CH2:28][N:23]3[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.C(N(CC)CC)C>CN(C=O)C.C(O[Cu]OC(=O)C)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([O:12][C:13]2[CH:14]=[CH:15][C:16]([C@@H:19]3[C:24]4=[N:25][S:26](=[O:30])(=[O:29])[CH2:27][CH2:28][N:23]4[CH2:22][CH2:21][CH2:20]3)=[CH:17][CH:18]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734352Boronic acid, (4-ethylphenyl)-HCID 66823991HCID 66823991, compound

Product 1

HCID 66823892HCID 66823892, compoundYield 7.7%

Reagents, catalysts & solvents 2

HCID 178476681HCID 178476681, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of (4-ethylphenyl)boronic acid (1.34 g), (9R)-9-(4-hydroxyphenyl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (500 mg), diacetoxycopper (648 mg), triethylamine (1.24 mL), and powdered 4A MS (1.50 g) in DMF (20 mL) was stirred at room temperature overnight. The mixture was added with NH silica gel, concentrated in vacuo, and purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) then recrystallized from EtOAc-IPE to give the title compound (53.0 mg) as a white solid.

Workup

  1. additionThe mixture was added with NH silica gel
  2. concentrationconcentrated in vacuo
  3. custompurified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  4. customthen recrystallized from EtOAc-IPE

Sources & evidence

ORD record
ord-d462f9187bfd48c79f2f25c32c9ff446
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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