Water → 5-(3-(4-isopropylpyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 634207Notes

Reaction equation

HRID 634207 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([NH:21][NH2:22])=[O:20])[CH:17]=3)[NH:12][CH:11]=2)[N:5]=1)([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.C1N=CN([C:37](N2C=NC=C2)=[O:38])C=1.O>CN(C=O)C>[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[O:20][C:37](=[O:38])[NH:22][N:21]=4)[CH:17]=3)[NH:12][CH:11]=2)[N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 683284933-(4-isopropylpyrimidin-2-yl)-1H-indole-5-carbohydrazide

Product 1

HCID 683284605-(3-(4-isopropylpyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-oneYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-isopropylpyrimidin-2-yl)-1H-indole-5-carbohydrazide (400 mg in about 60% pure) in DMF (3 mL) at RT was added N-ethyl-N-isopropylpropan-2-amine (0.47 mL, 2.71 mmol) followed by CDI (242 mg, 1.49 mmol). The mixture was stirred at RT for 5 min then heated in an oil bath at 65° C. for 1 h. It was cooled to RT, treated with 5 mL of H2O and extracted with 3×20 mL of EtOAc. The combine organic solution was washed with 3 mL of brine, dried and concentrated to afford 5-(3-(4-isopropylpyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (350 mg). This material was used in next step without further purification. MS (ESI, pos. ion) m/z: 322.0 (M+1).

Workup

  1. temperaturethen heated in an oil bath at 65° C. for 1 h
  2. temperatureIt was cooled to RT
  3. extractionextracted with 3×20 mL of EtOAc
  4. washThe combine organic solution was washed with 3 mL of brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bcb0a92f9dfc4303a8f214191aebe90b
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

Loading…