N-methyl-N-phenyl-2-(piperazin-1-yl)acetamide → 2-[4-(2-Amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-methyl-N-phenyl-acetamide

HRID 416699

反応式

HRID 416699 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3SC=CN=3)=[O:19])[CH2:13][CH2:12]2)[C:5]([Cl:26])=[CH:4][N:3]=1.NC1C([N+]([O-])=O)=C(Cl)C(Cl)=CN=1.CN([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)C(=O)CN1CCNCC1>C(O)(C)C>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([N:20]([CH3:21])[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:19])[CH2:13][CH2:12]2)[C:5]([Cl:26])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 2737187N-methyl-N-phenyl-2-(piperazin-1-yl)acetamideHCID 468676602-Amino-4,5-dichloro-3-nitropyridineHCID 468678042-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

生成物 1

HCID 578972912-[4-(2-Amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-methyl-N-phenyl-acetamide収率 57%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

The method followed that used to prepare 2-[4-(2-amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide (Example 6, Steps 1 to 6), but using 2-amino-4,5-dichloro-3-nitropyridine (0.036 g, 0.17 mmol), isopropanol (4.0 ml), and N-methyl-N-phenyl-2-piperazin-1-yl-acetamide (0.056 g, 0.24 mmol). Work-up and purification as described for 2-[4-(2-amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide afforded the title compound as an orange solid (0.039 g, 57%), 1H-NMR (500 Mz, DMSO-d6) 2.50 (obscured by DMSO peak, piperazine N(CH2)2), 2.96 (br s, 4H, piperazine N(CH2)2), 3.18 (s, 3H, NCH3), 6.94 (s, 2H, NH2), 7.35 (m, 3H) and 7.42 (m, 2H) (N-Ph), 8.05 (s, 1H, pyridine 6-H); LC-MS (ESI, m/z) 3.30 min—405, 407 [(M+H)+, Cl isotopic pattern].

後処理

  1. custompurification

出典と根拠

ORDレコード
ord-ffffa405208a46e68bad7d0f9c932074
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

関連ノート

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