Salicylamide → 2-[7-(2-Butynyl)-1-methyl-8-(3-methylaminopiperidin-1-yl)-6-oxo-6,7-dihydro-1H-purin-2-yloxy]benzamide hydrochloride

HRID 501426Notes

Reaction equation

[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10]([Cl:16])=[N:9][C:8]=2[N:7]=[C:6]1[N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([N:23]([CH3:31])C(=O)OC(C)(C)C)[CH2:18]1)[C:2]#[C:3][CH3:4].[OH:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([NH2:37])=[O:36].C(=O)([O-])[O-].[K+].[K+].Cl.NC1CCCN(C2N(CC#CC)C3C(=O)N(CC4C=CC=CC=4C#N)C(C#N)=NC=3N=2)C1>CN1CCCC1=O>[ClH:16].[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10]([O:32][C:33]3[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=3[C:35]([NH2:37])=[O:36])=[N:9][C:8]=2[N:7]=[C:6]1[N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([NH:23][CH3:31])[CH2:18]1)[C:2]#[C:3][CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture consisting of 20 mg of t-butyl N-[1-[7-(2-butynyl)-2-chloro-1-methyl-6-oxo-6,7-dihydro-1H-purin-8-yl]piperidin-3-yl]-N-methylcarbamate, 20 mg of 2-hydroxybenzamide, 20 mg of anhydrous potassium carbonate, and 0.3 ml of N-methyl-2-pyrrolidone was stirred in an oil bath at 80° C. for 4 hours. Subsequent synthesis steps were carried out according to the same procedure as used in Examples 242(f) and (g) to give the title compound.

Workup

customSubsequent synthesis steps

Sources & evidence

ORD record: ord-982186c7eb6b49938322553db68f6991
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772226B2

Reaction notes

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