Hydrochloric Acid → HCID 12805221, compound

HRID 1906235Notes

Reaction equation

HRID 1906235 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]([OH:26])=O)[CH:21]=2)[NH:16][CH:15]=1.C(OC(Cl)=O)C(C)C.[CH:35]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.Cl>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH:35]1([NH:41][C:24](=[O:26])[CH2:23][C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[CH2:13][CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 62365Isobutyl chloroformateHCID 12805187HCID 12805187, compound

Product 1

HCID 12805221HCID 12805221, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3-[2-(1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-acetic acid (0.2 g) and triethylamine (0.061 g) in chloroform (10 ml) was treated with isobutylchloroformate (0.08 g) at -5°, resulting red solution stirred at the same temperature for 20 h and cyclohexylamine was added to the resulting anhydride (0.06 g). Reaction was allowed to warm up to ambient temperature and stirred for 1 h then the mixture was poured into dilute hydrochloric acid (2N, 20 ml) extracted with chloroform (3×10 ml), dried (MgSO4), solvent removed and residual oil purified by chromatography (silica Merck, 7734; 10 g; 1% methanol in dichloromethane as eluent). Product was obtained as an oil which on treatment with ethyl acetate/ether gave the title compound as a solid (0.09 g) m.p. 175°-6°.

Workup

  1. customresulting red solution
  2. customReaction
  3. stirringstirred for 1 h
  4. extractionextracted with chloroform (3×10 ml)
  5. dry with materialdried (MgSO4), solvent
  6. customremoved
  7. customresidual oil purified by chromatography (silica Merck, 7734; 10 g; 1% methanol in dichloromethane as eluent)
  8. customProduct was obtained as an oil which on treatment with ethyl acetate/ether

Sources & evidence

ORD record
ord-6ae4f7c6d5874d10b79ddd3bebe72739
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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