1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59146071, compound

HRID 1512738Notes

Reaction equation

HRID 1512738 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:53])[C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[NH:44][C:43]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:42]2>CN(C=O)C>[Cl:22][C:23]1[CH:24]=[C:25]([C:26]2[O:28][N:53]=[C:38]([C:39]3[CH:40]=[C:41]4[C:45](=[CH:46][CH:47]=3)[NH:44][C:43]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:42]4)[N:37]=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 178468512HCID 178468512, compound

Product 1

HCID 59146071HCID 59146071, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

EDCI (144 mg) and HOBT (104 mg) were added to a solution of 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D32) (150 mg) in DMF (5 mL) at RT. The resulting solution was stirred for 15 min. Ethyl 5-[(hydroxyamino)(imino)methyl]-1H-indole-2-carboxylate (D22) (173 mg) was added and the reaction mixture was stirred at RT for 30 min. The reaction mixture was heated to 80° C. and stirred at that temperature for 5 hours. Most of the DMF was evaporated. EtOAc (50 mL) was added and the organic solution was washed with water (50 mL), saturated aqueous sodium bicarbonate solution (50 mL) and water (50 mL). The organic fraction was dried over anhydrous magnesium sulfate. The dried solution was concentrated. Trituration with ethanol provided ethyl 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-2-carboxylate (D23) (85 mg) as a yellow solid. δH (DMSO-d6, 400 MHz): 1.37 (9H, m), 4.38 (2H, q), 4.89 (1H, m), 7.35 (1H, d), 7.45 (1H, d), 7.62 (1H, d), 7.98 (1H, dd), 8.12 (1H, dd), 8.20 (1H, d), 8.49 (1H, d), 12.27 (1H, s). MS (ES): C22H20ClN3O4 requires 425; found 426.1 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred at RT for 30 min
  2. stirringstirred at that temperature for 5 hours
  3. customMost of the DMF was evaporated
  4. additionEtOAc (50 mL) was added
  5. washthe organic solution was washed with water (50 mL), saturated aqueous sodium bicarbonate solution (50 mL) and water (50 mL)
  6. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  7. concentrationThe dried solution was concentrated

Sources & evidence

ORD record
ord-de78591abf1646dd987417bf0da8dea5
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…