Diethylamine → 1-(Cyclohexyl)methyl-3-{5-[(diethylamino)methyl]-[1,3,4]-oxadiazol-2-yl}-7-methoxy-1H-indole, hydrochloride salt

HRID 644077Notes

Reaction equation

HRID 644077 reaction equation
[Cl:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[C:16]3[C:11](=[C:12]([O:17][CH3:18])[CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:9]=2)=[N:5][N:4]=1.[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>O1CCCC1>[ClH:1].[CH:20]1([CH2:19][N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])[C:8]([C:6]3[O:7][C:3]([CH2:2][N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])=[N:4][N:5]=3)=[CH:9]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 686961533-(5-chloromethyl-[1,3,4]oxadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole

Product 1

HCID 1317280761-(Cyclohexyl)methyl-3-{5-[(diethylamino)methyl]-[1,3,4]-oxadiazol-2-yl}-7-methoxy-1H-indole, hydrochloride saltYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-chloromethyl-[1,3,4]oxadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (92 mg, 0.26 mmol) in tetrahydrofuran (1 ml) was added diethylamine (0.134 ml, 1.28 mmol) and the reaction mixture subjected to microwave irradiation at 150° C. for 15 minutes. The resulting mixture was purified by flash column chromatography to afford the title compound (87 mg, 0.22 mmol) as the free base. The free base was dissolved in dichloromethane and hydrogen chloride (2M solution in diethyl ether; 1 ml, 2 mmol) was added. The excess reagent and solvent were removed by evaporation to the leave the title compound (1:1 hydrochloride salt) as a white solid. 1H NMR (400 MHz, CD3OD): 0.97-1.12 (2H, m), 1.15-1.26 (3H, m), 1.46 (6H, t, J 7), 1.53-1.63 (2H, m), 1.63-1.78 (3H, m), 1.8-1.95 (1H, m), 3.44 (4H, q, J 7), 3.98 (3H, s), 4.33 (2H, d, J 7), 4.84 (2H, s), 6.85 (1H, d, J 7), 7.19 (1H, t, J 7.9), 7.73 (1H, d, J 8), 7.94 (1H, s); EsIMS: m/z 397.1 [M+H]+, 324.4, 270.5.

Workup

  1. customirradiation at 150° C. for 15 minutes
  2. customThe resulting mixture was purified by flash column chromatography

Sources & evidence

ORD record
ord-f91a7128e1a14fb9a25a652ed3d573f1
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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