1-Butanol → 6-(4-Hydroxyphenyl)-1-(piperidin-3-ylmethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388141ノート

反応式

HRID 388141 の反応式
[NH2:1][C:2]1[C:3]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)=[N:4][C:5](Br)=[CH:6][N:7]=1.BrC1N=[C:27](N)[C:28](N)=NC=1.NCC1CCCN([C:41](OC(C)(C)C)=[O:42])C1.C(N(C(C)C)CC)(C)C.[CH2:57]([OH:61])[CH2:58][CH2:59][CH3:60]>>[OH:61][C:57]1[CH:28]=[CH:27][C:60]([C:5]2[N:4]=[C:3]3[N:9]([CH2:10][CH:11]4[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]4)[C:41](=[O:42])[NH:1][C:2]3=[N:7][CH:6]=2)=[CH:59][CH:58]=1

参加物

6

反応物 5

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 27564831-Boc-3-(aminomethyl)piperidineHCID 27718575-Bromopyrazine-2,3-diamineHCID 86626415tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylate

生成物 1

HCID 1358710236-(4-Hydroxyphenyl)-1-(piperidin-3-ylmethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one収率 61%

実験手順

tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylate. In a sealed tube, a solution of 5-bromopyrazine-2,3-diamine (1.88 g, 7.46 mmol), tert-butyl 3-(aminomethyl)piperidinecarboxylate (2.0 g, 9.33 mmol), diisopropylethylamine (1.95 mL, 11.19 mmol) in n-butanol (200 mL) was heated at 120° C. for 17 h. The volatiles were removed under reduced pressure. The residue was taken up in hexanes and sonicated. The resulting precipitate was collected by filtration to provide the title compound (1.7 g, 61%). MS (ESI) m/z 387.3 [M+1]+.

後処理

  1. customThe volatiles were removed under reduced pressure
  2. customsonicated
  3. filtrationThe resulting precipitate was collected by filtration

出典と根拠

ORDレコード
ord-52aa00ac4ee7497b874f39c5227c01b9
出典データセット
uspto-grants-2013_02
特許番号
US08372976B2

反応ノート

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