Triethylamine → 5-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

HRID 609737ノート

反応式

HRID 609737 の反応式
N[CH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][CH2:3]1.NC1CCC(C2C=C3C(=CC=2)NC=C3CCN2CCCC2)(O)CC1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl.C1COCC1.C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:5]1([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:6][CH2:7][CH2:2][CH2:3][CH:4]=1

参加物

9

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 699483875-(1-aza-1-methyl-4-hydroxycyclohex-4-yl)-3-(2-pyrrolidinylethyl)-1H-indoleHCID 699493865-(1-Aza-1-methylcyclohex-3-en-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole

生成物 1

HCID 699489945-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

試薬・触媒・溶媒 4

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-(1-Aza-1-methylcyclohex-3-en-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole: (17.6 mg, 13%) from 5-(1-aza-1-methyl-4-hydroxycyclohex-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 13d, 145 mg, 0.44 mmol), triethylamine (0.95 mL, 6.8 mmol) and MsCl (0.25 mL, 3.2 mmol) in dichloromethane (3.5 mL) and THF (7 mL) with the exception that the reaction was carried out at a gentle reflux overnight and the extraction solvent consisted of a mixture of dichloromethane, chloroform, and ethyl acetate. Starting material (17 mg) was also recovered. The product in this case was converted to the hydrochloride salt which was soluble in methanol; HRMS-FAB+ for C20H27N3 : calculated MH+ :310.22833; found MH+ :310.22650.

後処理

  1. temperaturea gentle reflux overnight
  2. customStarting material (17 mg) was also recovered

出典と根拠

ORDレコード
ord-4b3470229f6b48aea2f2e470c5a51fd0
出典データセット
uspto-grants-1999_12
特許番号
US05998438

反応ノート

読み込み中…