1-(1-Phenylethyl)piperazine → 5-Chloro-3-nitro-4-(4-(1-phenylethyl)piperazin-1-yl)pyridin-2-amine

HRID 416715

反応式

HRID 416715 の反応式
NC1C([N+]([O-])=O)=C(N2CCN(CC(NC3SC=CN=3)=O)CC2)C(Cl)=CN=1.[NH2:27][C:28]1[C:33]([N+:34]([O-:36])=[O:35])=[C:32](Cl)[C:31]([Cl:38])=[CH:30][N:29]=1.[C:39]1([CH:45]([N:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH3:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(O)(C)C>[Cl:38][C:31]1[C:32]([N:50]2[CH2:51][CH2:52][N:47]([CH:45]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH3:46])[CH2:48][CH2:49]2)=[C:33]([N+:34]([O-:36])=[O:35])[C:28]([NH2:27])=[N:29][CH:30]=1

参加物

5

反応物 3

HCID 27371341-(1-Phenylethyl)piperazineHCID 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 468683505-Chloro-3-nitro-4-(4-(1-phenylethyl)piperazin-1-yl)pyridin-2-amine収率 81.2%

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 1, step 5), but using 2-amino-4,5-dichloro-3-nitropyridine (0.034 g, 0.16 mmol), isopropanol (3.5 ml), and 1-(1-phenylethyl)piperazine (0.048 g, 0.25 mmol). Purification of the crude product on a silica isolute column using a gradient of ethyl acetate in dichloromethane as eluant (10 to 20%) afforded the title compound as a yellow solid (0.047 g, 81%). 1H-NMR (500 Mz, DMSO-d6) 1.30 (d, J=6.7 Hz, 3H, CH3), 2.40 (br s), and 2.53 (br s, obscured by DMSO peak) (4H, piperazine N(CH2)2), 3.03 (br s, 4H, piperazine N(CH2)2), 3.45 (m, 1H, NCHCH3), 6.98 (s, 2H, 2-NH2), 7.25 (m, 1H) and 7.32 (m, 2H) (ArH), 8.06 (s, 1H, 6-H);

後処理

  1. customPurification of the crude product on a silica isolute column

出典と根拠

ORDレコード
ord-1d8da34380f0465e989d6b508575b7b7
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

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