1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178472213, compound

HRID 1028214Notes

Reaction equation

HRID 1028214 reaction equation
C([CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:24][C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[F:34])=[O:26])[CH:20]=3)[CH2:15]2)=[O:13])[CH2:7][CH2:6]1)(O)=O.C[C:36]1([CH3:44])[O:43][C:41](=[O:42])[CH2:40][C:38](=[O:39])O1.CN(C1C=CC=CN=1)C.CCN=C=NCCCN(C)C>ClCCl>[CH2:36]([O:43][C:41]([CH2:40][C:38](=[O:39])[CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([O:11][C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:24][C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[F:34])=[O:26])[CH:20]=3)[CH2:15]2)=[O:13])[CH2:9][CH2:10]1)=[O:42])[CH3:44]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 218852-DimethylaminopyridineHCID 178525569HCID 178525569, compound

Product 1

HCID 178472213HCID 178472213, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane (10 mL) suspension of trans-6-[3-(2-fluoro-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 4-carboxymethyl-cyclohexyl ester (939 mg) obtained in Example 2, Meldrum's acid (317 mg), dimethylaminopyridine (293 mg), and EDCI (460 mg) were added at 0° C. The reaction mixture was diluted with dichloromethane, washed with 1 N hydrochloric acid and saturated brine, then dried over sodium sulfate, and then concentrated. A mixture of the residue and ethanol (10 mL) was heated to reflux for 4 hours and concentrated. The residue was purified by column chromatography (dichloromethane/ethyl acetate) to obtain the title compound (820 mg, 76%) as a yellowish-white solid.

Workup

  1. additionwere added at 0° C
  2. washwashed with 1 N hydrochloric acid and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. additionA mixture of the residue and ethanol (10 mL)
  6. temperaturewas heated
  7. temperatureto reflux for 4 hours
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-f87711f5afdd47cab35f70a5ad12f8c7
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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