Pyrrolidine → 1-(Cyclohexyl)methyl-7-methoxy-3-{5-[(pyrrolidin-1-yl)methyl]-[1,3,4]-thiadiazol-2-yl}-1H-indole, hydrochloride salt

HRID 644079Notes

Reaction equation

HRID 644079 reaction equation
[Cl:1][CH2:2][C:3]1[S: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.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>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[S:7][C:3]([CH2:2][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:4][N:5]=3)=[CH:9]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 687020533-(5-chloromethyl-[1,3,4]thiadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole

Product 1

HCID 1317280771-(Cyclohexyl)methyl-7-methoxy-3-{5-[(pyrrolidin-1-yl)methyl]-[1,3,4]-thiadiazol-2-yl}-1H-indole, hydrochloride saltYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-chloromethyl-[1,3,4]thiadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (93 mg, 0.25 mmol) in tetrahydrofuran was added pyrrolidine (0.101 ml, 1.235 mmol) and the mixture subjected to microwave irradiation at 150° C. for 5 minutes. The resulting reaction mixture was purified by flash column chromatography to give the title compound (42 mg, 0.1 mmol) as the free base. The free base was dissolved in dichloromethane and hydrogen chloride (1M solution in diethyl ether; 1 ml, 1 mmol) was added. The excess reagent and solvent were removed in vacuo to afford the title compound as a 1:1 hydrochloride salt.

Workup

  1. customirradiation at 150° C. for 5 minutes
  2. customThe resulting reaction mixture
  3. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-88350d5249dc4614aeb2630dfa731e93
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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