Triethylamine → HCID 86674506, compound

HRID 869681Notes

Reaction equation

HRID 869681 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([C:12]3[C:13]([CH3:22])=[N:14][C:15]4[C:20]([N:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:11]=[C:4]2[N:3]=1.[NH2:23][CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:5]2[N:9]=[C:10]([C:12]3[C:13]([CH3:22])=[N:14][C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:21]=3)[CH:11]=[C:4]2[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4192234-AminotetrahydropyranHCID 76683610HCID 76683610, compound

Product 1

HCID 86674506HCID 86674506, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(5,7-dichloropyrazolo[1,5-a]pyrimidin-2-yl)-2-methylquinoxaline (991 mg, 3.00 mmol), 4-aminotetrahydropyran (364 mg, 3.60 mmol), and triethylamine (1.25 mL, 9.00 mmol) in N,N-dimethylformamide (30 mL) was stirred for 2 h at room temperature. After being cooled to 0° C., the reaction mixture was diluted with water. The resulting precipitate was collected and purified by silica gel column chromatography (silica gel 200 g, chloroform to chloroform:ethyl acetate=1:1) to give 5-chloro-2-(3-methylquinoxalin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine. MS (APCI): m/z 395/397 (M+H).

Workup

  1. temperatureAfter being cooled to 0° C.
  2. customThe resulting precipitate was collected
  3. custompurified by silica gel column chromatography (silica gel 200 g, chloroform to chloroform:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b06b1bbeacef44599f94f5c8ef82e958
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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