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

HRID 1353838Notes

Reaction equation

HRID 1353838 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-fbae90af50474eb7adf9ad3a889d72e2
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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