3-Amino-4-picoline → 2-amino-N-(4-methylpyridin-3-yl)-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 869123Notes

Reaction equation

[NH2:1][C:2]1[C:14]([C:15]([O:17]N2C3C=CC=CC=3N=N2)=O)=[C:5]2[N:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][C:29]=1[NH2:34]>CN1C(=O)CCC1>[NH2:1][C:2]1[C:14]([C:15]([NH:34][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][C:28]=2[CH3:27])=[O:17])=[C:5]2[N:6]=[C:7]([C:10]([F:11])([F:12])[F:13])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of benzotriazol-1-yl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 6a (150 mg, 0.4129 mmol) in NMP (1.666 mL) was added 4-methylpyridin-3-amine (44.65 mg, 0.4129 mmol) and the reaction mixture was stirred at 100° C. for 17 hours in a sealed tube. The solid precipitate was filtered and dried under vacuum to afford the desired Compound I-C-1 as a yellow powder (60.4 mg, 42%). LC-MS (M+H)+ 337.2; 1H NMR (500 MHz, DMSO-d6) δ 9.45 (s, 1H), 9.40 (s, 1H), 9.30 (dd, J=6.9, 0.6 Hz, 1H), 8.22 (d, J=4.7 Hz, 1H), 7.52 (d, J=6.9 Hz, 1H), 7.33 (d, J=4.8 Hz, 1H), 7.01 (s, 2H), 2.42 (s, 3H).

Workup

filtrationThe solid precipitate was filtered
customdried under vacuum

Sources & evidence

ORD record: ord-cd0470ae910843a4bbce4107509771aa
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969360B2

Reaction notes

Loading…