Triethylamine → HCID 66824011, compound

HRID 1748080Notes

Reaction equation

HRID 1748080 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[OH:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]2[C:23]3=[N:24][S:25](=[O:29])(=[O:28])[CH2:26][CH2:27][N:22]3[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>CN(C=O)C.C(O[Cu]OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:11][C:12]1[CH:13]=[CH:14][C:15]([C@@H:18]2[C:23]3=[N:24][S:25](=[O:29])(=[O:28])[CH2:26][CH2:27][N:22]3[CH2:21][CH2:20][CH2:19]2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734323(3-Chlorophenyl)boronic acidHCID 66823991HCID 66823991, compound

Product 1

HCID 66824011HCID 66824011, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 178476681HCID 178476681, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chlorophenylboronic acid (167 mg), (9R)-9-(4-hydroxyphenyl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (100 mg), diacetoxycopper (130 mg), triethylamine (0.248 mL), and powdered 4A MS (1.50 g) in DMF (10 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) to give the title compound (32.0 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)

Sources & evidence

ORD record
ord-a1ab5c1e62a7462ba76abed6ff7c5228
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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