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

HRID 1014738노트

반응식

HRID 1014738 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-23dcaff612444a94bf2637ac2dc70151
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981893B2

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