Triethylamine → HCID 21190237, compound

HRID 1068753Notes

Reaction equation

HRID 1068753 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7]([S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])=[N:8]3.C(N(CC)CC)C.C1(N[S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])C=CC=CC=1>C(#N)C>[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7]([S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[N:8]3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 21190078HCID 21190078, compound

Product 1

HCID 21190237HCID 21190237, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 500 mg (1.82 mmol) of 3-methyl-2-[5-(amino)pentan-1-ylthio]-1,4,7b-triazacyclopent[cd]indene in 30 ml of acetonitrile were added 0.51 ml (3.66 mmol) of triethylamine and 1.302 g (3.66 mmol) of N-phenyltrifluoromethanesulfonamide. The mixture was stirred for two hours at room temperature. The solvent was distilled off. To the residue was added methylene chloride, which was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate) to afford 608 mg (82.1%, a pale yellow solid) of the desired compound.

Workup

  1. distillationThe solvent was distilled off
  2. additionTo the residue was added methylene chloride, which
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)
  7. customto afford 608 mg (82.1%

Sources & evidence

ORD record
ord-bcca444d0b844137b1b274f07f19e31e
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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