Methanesulfonyl chloride → HCID 86685429、化合物

HRID 1911034ノート

反応式

HRID 1911034 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:17]([CH2:21]O)=[C:16]([CH3:23])[C:15]=3[CH:24]=2)=[O:9])=[N:6][CH:7]=1.CS([Cl:29])(=O)=O.CCN(C(C)C)C(C)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:17]([CH2:21][Cl:29])=[C:16]([CH3:23])[C:15]=3[CH:24]=2)=[O:9])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 71060876HCID 71060876、化合物

生成物 1

HCID 86685429HCID 86685429、化合物収率 55.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-chloro-N-(8-(hydroxymethyl)-9-methyl-6,7-dihydro-5H-benzo[7]annulen-2-yl)picolinamide from step 3B (52 mg, 0.15 mmol) in dichloromethane (1 mL) was added methanesulfonylchloride (0.015 mL, 0.20 mmol) and DIPEA (0.048 mL, 0.27 mmol). The mixture was stirred at rt for 20 h. The mixture was subjected to chromatography (hexanes-100% EtOAc) to give 5-chloro-N-(8-(chloromethyl)-9-methyl-6,7-dihydro-5H-benzo[7]annulen-2-yl)picolinamide (30 mg, 0.083 mmol, 55% yield). LCMS (M+H)+=361.2. 1H NMR (500 MHz, chloroform-d) δ 9.81 (br. s., 1H), 8.58 (dd, J=2.3, 0.6 Hz, 1H), 8.27 (dd, J=8.4, 0.6 Hz, 1H), 7.90 (dd, J=8.4, 2.3 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 7.57 (dd, J=8.1, 2.3 Hz, 1H), 7.20 (d, J=8.1 Hz, 1H), 4.37 (s, 2H), 2.57 (t, J=7.0 Hz, 2H), 2.21 (s, 3H), 2.17 (quin, J=7.1 Hz, 2H), 2.05-1.98 (m, 2H)

出典と根拠

ORDレコード
ord-ef855cbad9aa4a19977cfedef9f3c9a6
出典データセット
uspto-grants-2013_12
特許番号
US08604024B2

反応ノート

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