Hydrochloric Acid → HCID 66917718, compound

HRID 1817987Notes

Reaction equation

HRID 1817987 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2/[CH:10]=[CH:11]/[C:12]([NH:14][S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:17])=[O:16])=[O:13])[CH:3]=[CH:2]1.S1C=CC=C1S(N)(=O)=O.Cl.CN(C)CCCN=C=NCC.N1C2C(=CC=CC=2C=CC(O)=O)C=C1.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[CH:11][C:12]([NH:14][S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:17])=[O:13])[CH:3]=[CH:2]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 728812-ThiophenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44627930HCID 44627930, compoundHCID 534015593-(1H-Indol-7-yl)prop-2-enoic acid

Product 1

HCID 66917718HCID 66917718, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Thiophene-2-sulfonic acid ((E)-3-1H-indol-7-yl-acryloyl)-amide (I-4) To a round bottom flask (500 mL) which contained a solution of thiophenesulfonamide (1.05 g, 6 mmol), 4-dimethyaminopyridine (DMAP, 1.56 g, 13 mmol) and 1-[3-(dimethyamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 2.4 g, 13 mmol) in CH2Cl2 (150 mL) was added 3-(1H-indol-7-yl)-acrylic acid I-3 (1.2 g, 6 mmol) at rt. The mixture which resulted was allowed to stir at rt for 72 h, then was cooled to 5° C. and was acidified with addition of aq HCl (10%) until pH=1, which was followed by extraction of CH2Cl2/MeOH (9/1, 3×100 mL). The combined organic layers were dried over anhyd. Na2SO4 and the solvent was removed under reduced pressure to provide the crude product which was purified by flash chromatography (silica gel, CH2Cl2; CH2Cl2/EtOAc/hexane=1:10:20-1:20:10) to afford desired thiophene-2-sulfonic acid (3-1H-indol-7-yl-acryloyl)-amide I-4 (1.2 g, 56%) as a white solid. MS(ESI−)m/z(331.1, 100%). LCMS(ESI−)>95%.

Workup

  1. customat rt
  2. customThe mixture which resulted
  3. temperaturewas cooled to 5° C.
  4. extractionwas followed by extraction of CH2Cl2/MeOH (9/1, 3×100 mL)
  5. customThe combined organic layers were dried over anhyd
  6. customNa2SO4 and the solvent was removed under reduced pressure
  7. customto provide the crude product which
  8. customwas purified by flash chromatography (silica gel, CH2Cl2; CH2Cl2/EtOAc/hexane=1:10:20-1:20:10)

Sources & evidence

ORD record
ord-3135b835b2784a5b85f59e12655ea227
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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