Hydrochloric Acid → HCID 66917833, compound

HRID 1817990Notes

Reaction equation

HRID 1817990 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[C:6](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)[CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[Cl:28][C:29]1[CH:30]=[C:31]([S:35]([NH2:38])(=[O:37])=[O:36])[S:32][C:33]=1[Cl:34].Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:5](=[C:6](/[CH:11]=[CH:12]/[C:13]([NH:38][S:35]([C:31]3[S:32][C:33]([Cl:34])=[C:29]([Cl:28])[CH:30]=3)(=[O:36])=[O:37])=[O:15])[CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37220944,5-Dichlorothiophene-2-sulfonamideHCID 44627932HCID 44627932, compound

Product 1

HCID 66917833HCID 66917833, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(E)-3-(3-Methyl-1H-indol-7-yl)-acrylic acid (I-7) (1 mmol), 4-dimethyaminopyridine (DMAP, 2 mmol) and 1-[3-(dimethyamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 2 mmol) in CH2Cl2 (30 mL) was added 4,5-dichloro-thiophene-2-sulfonic acid amide (1.1 mmol). The reaction mixture was stirred at room temperature for 24-40 hr. Recation mixture was diluted with another 30 ml of dichloromethane and then acidified with 10% aqueous HCl solution until pH˜1-2 (pH stripes). Organic layers was washed with saturated brine, dried over anhydrous Na2SO4 and concentrated 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 product, I-9. 1H-NMR (500 MHz, CDCl3) ESI M.S. gave (M−1): 436.4 with 88%.

Workup

  1. washOrganic layers was washed with saturated brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto provide the crude product which
  5. customwas purified by flash chromatography (silica gel, CH2Cl2; CH2Cl2/EtOAc/hexane=1:10:20-1:20:10)

Sources & evidence

ORD record
ord-e82ac1854bf24e4ea8f23188f701d06b
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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