1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57595486, compound

HRID 1785990Notes

Reaction equation

HRID 1785990 reaction equation
[C:1]([N:4]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:32]=[CH:31][C:20]([O:21][CH2:22][C:23]3[O:27][C:26]([C:28]([OH:30])=O)=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:33])[CH2:6]1)(=[O:3])[CH3:2].C1C=CC2N(O)N=[N:47]C=2C=1.CCN=C=NCCCN(C)C.[Cl-].[NH4+]>C1COCC1.CN(C=O)C.C(OCC)(=O)C>[C:1]([N:4]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:18]=[CH:19][C:20]([O:21][CH2:22][C:23]3[O:27][C:26]([C:28]([NH2:47])=[O:30])=[CH:25][CH:24]=3)=[CH:31][CH:32]=2)=[O:16])[C@@H:7]([CH3:33])[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 57595529HCID 57595529, compound

Product 1

HCID 57595486HCID 57595486, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S,4R)-5-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxymethyl)-furan-2-carboxylic acid (0.065 g, 0.12 mmol) was converted to the amide by dissolving in THF (1 mL) at room temperature. HOBt (0.024 g), EDCI (0.033 g), and ammonium chloride (0.013 g, 0.232 mmol) was added along with 2 drops of DMF and stirred at room temperature for 11 h. The reaction was diluted with ethyl acetate, washed with 1N NaOH, 1N HCl and brine. The organics were dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (10 ethyl acetate:1 methanol) to afford the product as a white solid in 61% yield.

Workup

  1. washwashed with 1N NaOH, 1N HCl and brine
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated down
  5. customThe crude residue was purified by silica gel chromatography (10 ethyl acetate:1 methanol)

Sources & evidence

ORD record
ord-0975063f50214ea4ad66ecdb8ca58fe1
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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