Hydrochloric Acid → HCID 59066225, compound

HRID 1006276Notes

Reaction equation

HRID 1006276 reaction equation
C([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([C:26]1[S:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[N:30]=1)=[C:6]([CH:24]=[O:25])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)[CH:14]=1)C.NC1C=CC=CC=1S.Cl.[CH3:44][CH2:45][OH:46]>>[CH2:45]([O:46][C:24]([C:6]1[N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH:21]3[CH2:22][CH2:23]3)[CH:14]=2)[C:8]2[C:4]([C:5]=1[C:26]1[S:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[N:30]=1)=[CH:3][CH:11]=[CH:10][CH:9]=2)=[O:25])[CH3:44]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 87132-AminothiophenolHCID 86587876HCID 86587876, compound

Product 1

HCID 59066225HCID 59066225, compoundYield 71%

Procedure

Ethyl-3-benzthiazol-2-yl-1-(3-cyclopropylmethoxybenzyl)-1H-indole-2-carboxaldehyde (Example 41, 0.42 g, 1.1 mmol) was taken up in EtOH (30 mL) at room temperature. 2-aminothiophenol (0.15 g, 1.05 eq.) was added, followed by conc. HCl (0.5 mL), and the reaction mixture was heated to reflux for 24 hours. The mixture was cooled to room temperature, quenched with water and extracted with diethyl ether (3×50 mL.) The organic layers were separated, dried over sodium sulfate, and concentrated in vacuo to give the desired product (0.38 g, 71%) which was taken to the hydrolysis step without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. customquenched with water
  4. extractionextracted with diethyl ether (3×50 mL.) The organic layers
  5. customwere separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e67e899c6c454cd294f212a14cea562e
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

Loading…