Water → HCID 12822470, compound

HRID 980290Notes

Reaction equation

HRID 980290 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29].O.[Cl-].[Na+]>N1C=CC=CC=1.Cl>[O:29]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[N:19]1[CH2:18][CH2:17][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:9]=2)[NH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 31297Methanesulfonyl chloride2×HCID 12803116HCID 12803116, compound

Product 1

HCID 12822470HCID 12822470, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.23 ml) was added to an ice cooled, stirred solution of 2-[2-[5-(aminomethyl)-1H-indole-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione, hemisulphate, hydrate (0.84 g) in dry pyridine (25 ml). After 20 h at room temperature, a further portion of methanesulphonyl chloride (0.14 ml) was added. The mixture was stirred for 2 h, water (10 ml) was added and the solution was stirred for a further 1 h. The solution was diluted with hydrochloric acid (2N; 250 ml) containing sodium chloride (30 g) and ice. The product was extracted into ethyl acetate (2×80 ml) and the extract was washed with brine (2×60 ml), dried (Na2SO4) and evaporated in vacuo to leave a yellow foam (0.85 g).

Workup

  1. temperaturecooled
  2. stirringthe solution was stirred for a further 1 h
  3. extractionThe product was extracted into ethyl acetate (2×80 ml)
  4. washthe extract was washed with brine (2×60 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-efcc58f0ade94da8819dd46a689189a0
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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