Tetrahydrofuran → 1-perhydro-2H-pyran-2-yl-3-[3-(3-pyridylcarbonylamino)phenyl]-1H-indazole-5-carboxamide

HRID 1349781Notes

Reaction equation

HRID 1349781 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1.C(N(CC)CC)C.[O:42]1CCCC1>>[O:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:19]1[N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]([NH2:18])=[O:42])=[CH:13][CH:12]=2)[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:26]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:33])[CH:3]=2)=[N:9]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 22480146HCID 22480146, compound

Product 1

HCID 224802181-perhydro-2H-pyran-2-yl-3-[3-(3-pyridylcarbonylamino)phenyl]-1H-indazole-5-carboxamide

Procedure

To a solution of 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.150 g, 0.47 mmol) in tetrahydrofuran (5 mL), was added nicotinoyl chloride hydrochloride (0.167 mg, 0.94 mmol) and triethyl amine (0.327 mL, 2.35 mmol). After stirring at room temperature overnight, the crude mixture was partitioned between ethyl acetate and water. The crude compound was isolated as a gummy solid. The yield was not calculated: ES-MS (m/z) 424 [M+H]+.

Workup

  1. customthe crude mixture was partitioned between ethyl acetate and water

Sources & evidence

ORD record
ord-71768dd3a6f84c7db389c3924eb211b1
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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