Triethylamine → HCID 68328255, compound

HRID 634337Notes

Reaction equation

HRID 634337 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[C:43]([C:46]3[O:50][C:49]([NH:51][CH:52]([CH3:54])[CH3:53])=[N:48][N:47]=3)[CH:44]=2)[NH:39][CH:38]=1>CN(C=O)C>[CH:52]([NH:51][C:49]1[O:50][C:46]([C:43]2[CH:44]=[C:45]3[C:40](=[CH:41][CH:42]=2)[NH:39][CH:38]=[C:37]3[NH:36][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:6])=[N:47][N:48]=1)([CH3:54])[CH3:53]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68328171HCID 68328171, compound

Product 1

HCID 68328255HCID 68328255, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclopropanecarboxylic acid (55 mg, 0.642 mmol) in DMF (6 mL) was added EDC.HCl (167 mg, 0.875 mmol), HOBt (118 mg, 0.875 mmol) and triethylamine (0.244 mL, 1.75 mmol). The mixture was stirred for 15 min, then 5-(3-amino-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (150 mg, 0.583 mmol) was added and the mixture was stirred for 16 h at RT. The reaction was quenched with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified with basic alumina chromatography to give N-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)cyclopropane carboxamide (21 mg, 11%). MS (ESI, pos. ion) m/z: 326.2 (M+1); 1H-NMR (300 MHz, DMSO-d6): δ 11.13 (s, 1H), 10.43 (s, 1H), 8.37 (brs, 1H), 7.75 (d, 1H, J=2.1 Hz), 7.41-7.55 (m, 3H), 3.70-3.76 (m, 1H), 1.92-1.97 (m, 1H), 1.21 (d, 6H, J=6.6 Hz), 0.77-0.79 (m, 4H).

Workup

  1. stirringthe mixture was stirred for 16 h at RT
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with basic alumina chromatography

Sources & evidence

ORD record
ord-59d31c10aa024b8f9c027a3430227c88
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

Loading…