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

HRID 1272923Notes

Reaction equation

HRID 1272923 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-122eef18e63e4222bef5b1e214da2d2d
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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