1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 882999-52-2

HRID 2106064Notes

Reaction equation

HRID 2106064 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:16].[Cl:17][C:18]1[CH:19]=[C:20]([S:24]([NH2:27])(=[O:26])=[O:25])[S:21][C:22]=1[Cl:23].CCN=C=NCCCN(C)C>CN(C)C1C=CN=CC=1.ClCCl.Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9](/[CH:11]=[CH:12]/[C:13]([NH:27][S:24]([C:20]3[S:21][C:22]([Cl:23])=[C:18]([Cl:17])[CH:19]=3)(=[O:25])=[O:26])=[O:15])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:16]

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 37220944,5-Dichlorothiophene-2-sulfonamideHCID 57810467HCID 57810467, compound

Product 1

HCID 57810472882999-52-2Yield 71%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (E)-3-(5-fluoro-3-methyl-1H-indol-7-yl)-acrylic acid (772 g, 3.53 mole), 4,5-dichloro-2-thiophenesulfonamide (900 g, 3.88 mole), 4-(dimethylamino)pyridine (861 g, 7.06 mole) and EDCI (1.348 kg, 7.06 mole) in dichloromethane (25.5 L) was stirred at ambient temperature for 14 h. The solution was diluted with 2 M aqueous HCl (16 L), and stirred for 1.5 h, which induced precipitation of the product. The product was collected via vacuum filtration and washed sequentially with water (2×2 L), dichloromethane (2×2 L), and hexanes (2 L) to provide 1.044 kg (71% yield) of the desired title compound. 1H NMR (400 MHz, DMSO-d6) δ 2.23 (s, 3H), 6.71 (d, 1H, J=15.6 Hz), 7.22 (dd, 1H, J=10.0, 2.6 Hz), 7.27 (br s, 1H), 7.39 (dd, 1H, J=9.6, 2.6 Hz), 7.95 (s, 1H), 8.15 (dd, 1H, J=15.6, 1.2 Hz), 11.35 (s, 1H).

Workup

  1. stirringstirred for 1.5 h
  2. customprecipitation of the product
  3. filtrationThe product was collected via vacuum filtration
  4. washwashed sequentially with water (2×2 L), dichloromethane (2×2 L), and hexanes (2 L)

Sources & evidence

ORD record
ord-2a96a73eb8f64bb1950cb2fb658f5c92
Source dataset
uspto-grants-2009_08
Patent number
US07579483B2

Reaction notes

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