2,4-Dichlorobenzoyl chloride → 2,4-Dichloro-N-{[4-(morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidin-4-yl]methyl}benzamide

HRID 2102391ノート

反応式

HRID 2102391 の反応式
[N:1]1([C:7]([C:9]2([CH2:21][NH2:22])[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH3:20])(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[Cl:32][C:33]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>C(Cl)Cl>[Cl:32][C:33]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:34]=1[C:35]([NH:22][CH2:21][C:9]1([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:8])[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH3:20])(=[O:17])=[O:16])[CH2:11][CH2:10]1)=[O:36]

参加物

5

反応物 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 57803091{[4-(Morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidin-4-yl]methyl}amine

生成物 1

HCID 116990682,4-Dichloro-N-{[4-(morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidin-4-yl]methyl}benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of {[4-(morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidin-4-yl]methyl}amine (I-5) (33 mg, 0.10 mmole), DIEA (35 μL, 0.20 mmole), and 2,4-dichlorobenzoyl chloride (23 mg, 0.11 mmole) in DCM (2 mL) was shaken 1 h at room temperature. After this time, LCMS indicated that the reaction was completion. DCM was removed by nitrogen gas flow and the residue was purified by LCMS to afford the title compound (I-6) as a white solid. Analytical LCMS: single peak (214 nm), 2.867 min. 1H NMR (600 MHz, CD3CN): δ 7.52 (dd, J=0.9, 1.5 Hz, 2H), 7.39 (m, 2H), 6.98 (t, J=5.9 Hz, 1H), 3.63 (m, 10H), 3.49 (m, 2H), 3.05 (m, 2H), 2.89 (t, J=7.8 Hz, 2H), 2.30 (m, 2H), 1.74 (m, 2H), 1.62 (m, 2H), 1.01 (t, J=7.4 Hz, 3H); HRMS: calc'd for C21H29Cl2N3O5S [M+H], 506.1278; found 506.1248.

後処理

  1. customDCM was removed by nitrogen gas flow
  2. customthe residue was purified by LCMS

出典と根拠

ORDレコード
ord-8096b9c7f6784d6a8ce0f6655b1b0f9b
出典データセット
uspto-grants-2009_08
特許番号
US07576083B2

反応ノート

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