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Hydrochloric Acid → [3-Amino-6-(3,4-dichloro-phenyl)-pyrazin-2-yl]-(4-piperidin-1-ylmethyl-phenyl)-methanone

HRID 81463
ノート
印刷プレビュー

反応式

HRID 81463 の反応式
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CON(C)[C:19]([C:21]1[C:26]([NH2:27])=[N:25][CH:24]=[C:23]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[N:22]=1)=[O:20].Cl>C1COCC1>[NH2:27][C:26]1[C:21]([C:19]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:9][CH:10]=2)=[O:20])=[N:22][C:23]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)=[CH:24][N:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 866345423-Amino-6-(3,4-dichloro-phenyl)-pyrazine-2-carboxylic acid methoxy-methyl amide2 回HCID 178419630HCID 178419630、化合物

生成物 1

HCID 44233342[3-Amino-6-(3,4-dichloro-phenyl)-pyrazin-2-yl]-(4-piperidin-1-ylmethyl-phenyl)-methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 0.25 M [4-(1-piperidinyl-methyl)phenyl]magnesium bromide in THF (5.51 ml, 1.37 mmol) is added dropwise to a solution of 3-amino-6-(3,4-dichloro-phenyl)-pyrazine-2-carboxylic acid methoxy-methyl amide (Intermediate B) (0.09 g, 0.27 mmol) in THF (5 ml) and the resulting solution is stirred for 2 hours. The solution is cooled to 0° C., and 2M HCl (10 ml) is added. The solution is washed with EtOAc (20 ml) and then the pH is adjusted to 11 using 2M NaOH. Extraction with EtOAc (50 ml), drying (MgSO4) and removal of solvent in vacuo affords a yellow oil. Purification by flash chromatography (SiO2, 50-100% EtOAc in iso-hexane) followed by trituration with methanol affords the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-6) δ 9.04 (1H, s), 8.12 (1H, d), 7.97 (2H, bs), 7.93-7.88 (3H, m), 7.71 (1H, d), 7.47 (2H, d), 3.54 (2H, s), 2.36 (4H, bs), 1.52-1.51 (4H, m), 1.43-1.37 (2H, m); MS m/z 441, 443 [M+H]+

後処理

  1. washThe solution is washed with EtOAc (20 ml)
  2. extractionExtraction with EtOAc (50 ml)
  3. customdrying
  4. custom(MgSO4) and removal of solvent in vacuo
  5. customaffords a yellow oil
  6. customPurification by flash chromatography (SiO2, 50-100% EtOAc in iso-hexane)

出典と根拠

ORDレコード
ord-5955e02f18954e03bc3695ee92def8e7
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846687B2

反応ノート

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