Methylamine → HCID 11597073, compound

HRID 2099233Notes

Reaction equation

[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:31])=[C:11]([N:13]3[CH:21]=[N:20][C:19]4[C:14]3=[N:15][CH:16]=[N:17][C:18]=4[C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=3)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.CN.O[N:35]1[C:39]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:8]=[CH:9][C:10]([CH3:31])=[C:11]([N:13]3[CH:21]=[N:20][C:19]4[C:14]3=[N:15][CH:16]=[N:17][C:18]=4[C:22]3[CH:30]=[CH:29][C:25]([C:26](=[O:28])[NH:35][CH3:39])=[CH:24][CH:23]=3)[CH:12]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of the 4-[9-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-9H-purin-6-yl]-benzoic acid (10 mg, 0.024 mmol) and the methyl amine (3.0 mg, 0.097 mmol) in 0.5 mL of dry DMF was added 1-hydroxybenzotriazole (7.4 mg, 0.048 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.2 mg, 0.048 mmol) at 20° C. The reaction mixture was stirred at 20° C. for 4 hours. And then 2 mL of water was added. The product was collected by filtration to give a colorless solid (8.2 mg, 80%). HPLC tR=1.99 min; MS m/z 427 [M+H]+.

Workup

filtrationThe product was collected by filtration

Sources & evidence

ORD record: ord-9dceab6c1110487e998cc9710735db26
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569571B2

Reaction notes

Loading…