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

HRID 1014738Notes

Reaction equation

HRID 1014738 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-23dcaff612444a94bf2637ac2dc70151
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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