Isopropylamine → 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

HRID 634102Notes

Reaction equation

HRID 634102 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[O:21][C:20]([NH:22][CH2:23][C:24]5[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=5)=[N:19][N:18]=4)[CH:15]=3)[N:10]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:9]=2)[N:3]=1.[CH:42]([NH2:45])([CH3:44])[CH3:43]>CS(C)=O>[CH:42]([NH:45][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[O:21][C:20]([NH:22][CH2:23][C:24]5[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=5)=[N:19][N:18]=4)[CH:15]=3)[N:10]([S:32]([C:35]3[CH:36]=[CH:37][C:38]([CH3:39])=[CH:40][CH:41]=3)(=[O:33])=[O:34])[CH:9]=2)[N:3]=1)([CH3:44])[CH3:43]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 867250935-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 683285465-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amineYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (500 mg, 0.85 mmol) in DMSO (5 mL) was added isopropylamine (60 mg, 1.02 mmol). The mixture was stirred at 110° C. for 12 h. The reaction was quenched with ice cold H2O and was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified with flash chromatography (basic alumina, eluting with 30-40% EtOAc in Hex) to give 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (220 mg, 52%). MS (ESI, pos. ion) m/z: 609.6 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 9.07 (s, 1H), 8.39 (s, 1H), 8.23 (m, 1H), 8.12 (d, J=8 Hz, 1H), 8.00 (d, J=8 Hz, 2H), 7.85 (d, J=8.4 Hz, 1H), 7.79-7.57 (m, 5H), 7.43 (d, J=8 Hz, 2H), 7.312 (d, J=8 Hz, 3H), 6.90 (d, J=8 Hz, 2H), 4.38 (m, 3H), 3.72 (s, 3H), 2.32 (s, 3H), 1.17 (d, J=6.4 Hz, 6H).

Workup

  1. customThe reaction was quenched with ice cold H2O
  2. extractionwas extracted with EtOAc
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with flash chromatography (basic alumina, eluting with 30-40% EtOAc in Hex)

Sources & evidence

ORD record
ord-ec217a58b0364ee4948ea54c73c30127
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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