1-Butanol → N-Methyl-4-(2-oxo-3-((tetrahydro-2H-pyran-4-YL)methyl)-2,3-dihydro-1H-imidazo[4,5-B]pyrazin-5-YL)benzamide

HRID 1014701Notes

Reaction equation

HRID 1014701 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:5]([NH2:16])=[N:4][CH:3]=1.BrC1N=[C:20]([NH2:25])C(N)=NC=1.[O:26]1CCC(CN)C[CH2:27]1.[CH:34](N(C(C)C)CC)([CH3:36])[CH3:35].[CH2:43]([OH:47])[CH2:44][CH2:45][CH3:46]>>[CH3:20][NH:25][C:43](=[O:47])[C:44]1[CH:36]=[CH:34][C:35]([C:2]2[N:7]=[C:6]3[N:8]([CH2:9][CH:10]4[CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)[C:27](=[O:26])[NH:16][C:5]3=[N:4][CH:3]=2)=[CH:46][CH:45]=1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 27718575-Bromopyrazine-2,3-diamineHCID 27732104-AminomethyltetrahydropyranHCID 86626394HCID 86626394, compound

Product 1

HCID 24984055N-Methyl-4-(2-oxo-3-((tetrahydro-2H-pyran-4-YL)methyl)-2,3-dihydro-1H-imidazo[4,5-B]pyrazin-5-YL)benzamideYield 64%

Procedure

6-Bromo-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine. In a sealed tube, a solution of 5-bromopyrazine-2,3-diamine (6.98 g, 2.78 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (4.0 g, 3.47 mmol), diisopropylethylamine (6.06 mL, 3.47 mmol) in n-butanol (100 mL) was heated at 120° C. for 17 h. The volatiles were removed under reduced pressure. The residue was taken up in hexanes/diethylether and sonicated. The resulting precipitate was collected by filtration to provide the desired product (5.10 g, 64% yield). MS (ESI) m/z 289.1 [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-dedf56c382324600890c21a6f8b28816
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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