Diisopropylethylamine → (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-((R)-1-benzyl-piperidin-3-yl)amine

HRID 1257574

反応式

[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18](Cl)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH2:36])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C>CC(O)C.C(Cl)Cl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18]([NH:36][C@@H:32]4[CH2:33][CH2:34][CH2:35][N:30]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:31]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

反応条件

温度: 120 °C

実験手順

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (260 mg, 0.77 mmol), (R)-1-benzyl-3-aminopiperidine (175 mg, 0.92 mmol), diisopropylethylamine (197 μl, 1.16 mmol) in propan-2-ol (5 ml) was heated in a microwave reactor at 120° C. for 10 minutes. The mixture was diluted with DCM and then purified by column chromatography on silica gel (gradient: 0 to 40% ethyl acetate in cyclohexane) affording 429 mg of (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-((R)-1-benzyl-piperidin-3-yl)amine, which was used for the next step without further purification. LCMS (Method B, ESI): RT=3.58 min, m+H=492.5; 1H NMR (400 MHz, CDCl3) δ: 9.53 (br s, 1H), 9.10 (s, 1H), 8.19-8.15 (m, 2H), 7.69-7.33 (m, 9H), 6.68-6.61 (m, 1H), 4.24-4.15 (br m, 1H), 3.54 (s, 2H), 2.77-2.27 (br m, 4H), 1.88-1.74 (br m, 3H), 1.69-1.52 (br m, 1H).

後処理

custompurified by column chromatography on silica gel (gradient: 0 to 40% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード: ord-f5edf8df77a6477f8499dd3e311491e7
出典データセット: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08461328B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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