1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59316697, compound

HRID 2189786Notes

Reaction equation

HRID 2189786 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:3].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O[NH:40][C:41](=[NH:58])[C:42]1[CH:43]=[C:44]2[C:48](=[CH:49][CH:50]=1)[N:47]([CH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[N:46]=[CH:45]2.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]2[O:11][N:40]=[C:41]([C:42]3[CH:43]=[C:44]4[C:48](=[CH:49][CH:50]=3)[N:47]([CH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[N:46]=[CH:45]4)[N:58]=2)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:1]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide3×HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 225977674-Isopropoxy-3-(trifluoromethyl)benzoic acidHCID 178471847HCID 178471847, compound

Product 1

HCID 59316697HCID 59316697, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)benzoic acid (D36) (100 mg, 0.4 mmol) was dissolved in DMF (5 ml) and then EDAC (115 mg, 0.6 mmol) and HOBt (81 mg, 0.6 mmol) were added. The mixture was stirred for 30 minutes and then Ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}propanoate (D52) (111 mg, 0.40 mmol) was added and the reaction was heated overnight at 80° C. Further EDAC (50 mg) was added and the reaction was heated for another 4 hours. Further EDAC (20 mg) was added and the reaction was heated overnight. The reaction mixture was added to a mixture of ethyl acetate and sodium bicarbonate, the organics were separated and the aqueous extracted with further ethyl acetate. The combined organics were washed with water and then brine, dried and evaporated to give the crude product. This material was purified by flash chromatography (SiO2) to afford the title compound (82 mg). MS (ES): C24H23F3N4O4 requires 488; found (MH+) 489.

Workup

  1. temperaturethe reaction was heated for another 4 hours
  2. temperaturethe reaction was heated overnight
  3. customthe organics were separated
  4. extractionthe aqueous extracted with further ethyl acetate
  5. washThe combined organics were washed with water
  6. dry with materialbrine, dried
  7. customevaporated
  8. customto give the crude product
  9. customThis material was purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-b40f82f8e66148fea061d23b9f40db99
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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