Triethylamine → HCID 178465594, compound

HRID 2356979Notes

Reaction equation

HRID 2356979 reaction equation
Cl.[C:2]1([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][NH2:22])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([N:25](CC)CC)[CH3:24]>C(O)C>[C:2]1([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][NH:22][C:23](=[NH:25])[CH3:24])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 68459548HCID 68459548, compound

Product 1

HCID 178465594HCID 178465594, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

C-(7-Benzenesulfonyl-chroman-4-yl)-methylamine HCl salt (90 mg, 0.26 mmol) and methyl imidate (acetimidic acid methyl ester, 58 mg, 0.529 mmol) were dissolved in 3 mL of absolute ethanol and 0.362 mL of triethylamine (2.6 mmol) was added. The reaction mixture was stirred at 80° C. for 2 days. It was then cooled, partitioned between EtOAc and water, dried over MgSO4 concentrated and purified using column chromatography (silica gel, MeOH/CHCl3/NH4OH 10:89:1) After formation of the HCl salt, 9 mg (10%) of. N-(7-Benzenesulfonyl-chroman-4-ylmethyl)-acetamidine was collected. MS: 345 (M+H)+.

Workup

  1. temperatureIt was then cooled
  2. custompartitioned between EtOAc and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified
  6. customN-(7-Benzenesulfonyl-chroman-4-ylmethyl)-acetamidine was collected

Sources & evidence

ORD record
ord-d22973542ede448ab01c3e5e14a14730
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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