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

HRID 644079
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HRID 644079 반응식
[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
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HCID 31268PyrrolidineHCID 687020533-(5-chloromethyl-[1,3,4]thiadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-88350d5249dc4614aeb2630dfa731e93
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07700634B2

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