1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59146052, compound

HRID 1512732Notes

Reaction equation

HRID 1512732 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH:33]([CH3:35])[CH3:34])[C:26]([OH:28])=O.O[NH:37][C:38](=[NH:57])[C:39]1[CH:47]=[C:46]2[C:42]([C:43]([CH2:48][CH2:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[CH:44][NH:45]2)=[CH:41][CH:40]=1>CN(C=O)C>[Cl:22][C:23]1[CH:24]=[C:25]([C:26]2[O:28][N:37]=[C:38]([C:39]3[CH:47]=[C:46]4[C:42]([C:43]([CH2:48][CH2:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[CH:44][NH:45]4)=[CH:41][CH:40]=3)[N:57]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH:33]([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178450933HCID 178450933, compound

Product 1

HCID 59146052HCID 59146052, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

EDCI (297 mg) and HOBT (237 mg) were added to a solution of 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D32) (277 mg) in DMF (10 mL) at RT. The resulting solution was stirred for 10 min. A solution of 1,1-Dimethylethyl 3-{6-[(hydroxyamino)(imino)methyl]-1H-indol-3-yl}propanoate (D16) (392 mg) in DMF (10 mL) was added and the reaction mixture was stirred at RT for 1 hour. The reaction mixture was heated to 80° C. and stirred at that temperature for 8 hours, then standed at RT for overweekend. The reaction mixture was heated to 80° C. for 2 hours. Most of the DMF was evaporated. EtOAc (100 mL) was added and the organic solution was washed with saturated aqueous sodium bicarbonate solution (100 mL) and water (100 mL). The organic fraction was dried over anhydrous magnesium sulfate. The dried solution was concentrated. The residue was purified by Biotage (25% EtOAc in hexane) to afford 1,1-dimethylethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D17) (314 mg) as a white solid. MS (ES): C26H28ClN3O4 requires 481; found 482.0 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred at RT for 1 hour
  2. stirringstirred at that temperature for 8 hours
  3. customstanded at RT for overweekend
  4. temperatureThe reaction mixture was heated to 80° C. for 2 hours
  5. customMost of the DMF was evaporated
  6. additionEtOAc (100 mL) was added
  7. washthe organic solution was washed with saturated aqueous sodium bicarbonate solution (100 mL) and water (100 mL)
  8. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  9. concentrationThe dried solution was concentrated
  10. customThe residue was purified by Biotage (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-f117c757b7054065af8e34e9d6600d52
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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