1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178513917, compound

HRID 1028205Notes

Reaction equation

HRID 1028205 reaction equation
[C:1]([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.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[OH2:56].[NH3:57]>C(OCC)(=O)C.CN(C=O)C>[C:1]([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:56])[NH2:57]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 12896473Azane;hydrateHCID 178525569HCID 178525569, compound

Product 1

HCID 178513917HCID 178513917, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A DMF (15 mL) solution of trans-6-[3-(2-fluoro-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 4-carboxymethyl-cyclohexyl ester (527 mg) obtained in Example 2, HOBt (166 mg), EDCI (236 mg), and ammonia water (0.5 mL) was stirred at room temperature for 2 days. The reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried, and concentrated. The residue was purified by chromatography (NH silica gel, dichloromethane/methanol=30:1→5:1) to obtain a solid. This solid was recrystallized (isopropanol) to obtain the title compound (89 mg, 17%) as a white solid.

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate and saturated brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (NH silica gel, dichloromethane/methanol=30:1→5:1)
  5. customto obtain a solid
  6. customThis solid was recrystallized (isopropanol)

Sources & evidence

ORD record
ord-c642499edd304c98907d1c4756a73348
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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