Hydrochloric Acid → HCID 12822476, compound

HRID 980295Notes

Reaction equation

HRID 980295 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[F:25][C:26]([F:32])([F:31])[S:27](Cl)(=[O:29])=[O:28].O.Cl>N1C=CC=CC=1>[O:23]=[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:24])[N:14]1[CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][NH:1][S:27]([C:26]([F:32])([F:31])[F:25])(=[O:29])=[O:28])[CH:4]=2)[NH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 79000Trifluoromethanesulfonyl chloride2×HCID 12803116HCID 12803116, compound

Product 1

HCID 12822476HCID 12822476, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 2-[2-(5-aminomethyl-1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione, hemisulphate, hydrate (1.10 g) in pyridine (40 ml) was cooled in an icebath and treated dropwise with trifluoromethanesulphonyl chloride (0.5 ml). The mixture was stirred at room temperature for 5.5 h, further trifluoromethanesulphonyl chloride (0.5 ml) being added after 4.75 h, and water (10 ml) was added. After 10 minutes the solution was acidified with hydrochloric acid (2N) and extracted into ethyl acetate (4×100 ml). The combined extract was washed with sodium carbonate (2N; 100 ml), dried (magnesium sulphate) and evaporated to dryness, affording a yellow-brown foam (1.2 g). This was purified by chromatography on a silica column (Merck Kieselgel 60; 22 g) eluted with ethyl acetate, affording title material as a yellow-brown solid (0.91 g), m.p. 176°-8°.

Workup

  1. temperaturewas cooled in an icebath
  2. extractionextracted into ethyl acetate (4×100 ml)
  3. extractionThe combined extract
  4. washwas washed with sodium carbonate (2N; 100 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b9fa20d1d075454785728aaaa2786c47
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

Loading…