Methanesulfonyl chloride → (5-Chloromethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine

HRID 1170133ノート

反応式

HRID 1170133 の反応式
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19]O)[N:10]=2)=[CH:4][CH:3]=1.CS([Cl:25])(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[Cl:25][CH2:19][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[CH:17]=[CH:18][C:9]([NH:8][CH2:7][C:5]1[O:6][C:2]([CH3:1])=[CH:3][CH:4]=1)=[N:10]2

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 44218152{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol

生成物 1

HCID 68436366(5-Chloromethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol (example 41, step A, 70 mg, 0.261 mmol) was dissolved in 2 mL tetrahydrofurane and methanesulfonyl chloride (34 mg, 0.297 mmol) and N,N-diisopropyl ethyl amine (41 mg, 0.318 mmol) were added. The reaction mixture was stirred at room temperature overnight and the solvent was evaporated off. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). (5-Chloromethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine was obtained as a brown solid (59 mg, 79%), MS: m/e=287.0 (M+H+).

後処理

  1. customthe solvent was evaporated off
  2. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

出典と根拠

ORDレコード
ord-e2cac7a370c34b74b95a55a09558e1dd
出典データセット
uspto-grants-2010_11
特許番号
US07825253B2

反応ノート

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