Diisopropylethylamine → HCID 24873257, compound

HRID 2106289Notes

Reaction equation

HRID 2106289 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CCN(C(C)C)C(C)C.[CH:41]1[CH:46]=[CH:45][C:44](N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=[CH:43][CH:42]=1>C(Cl)Cl>[C:18]1([N:13]2[C:12]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[C:11]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]3)=[N:14]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 86598385HCID 86598385, compound

Product 1

HCID 24873257HCID 24873257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. To a stirred solution of the above compound (1.79 g) in 35 mL of CH2Cl2 was added 3.0 mL of i-Pr2NEt and 3.05 g of N-phenyltrifluoromethanesulfonimide. The mixture was heated at reflux for 24 h and then was concentrated in vacuo. Chromatography on SiO2 (0 to 75% EtOAc/hexanes) afforded 1.88 g of the desired compound. MS (ESI): exact mass calculated for C19H22F3N3O5S, 461.12; found, m/z 407.1 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-b351b803690d4ecabdca38d9bf5f7f8a
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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