Pyridinium, 1-amino-, iodide (1:1) → N-[5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide

HRID 1157640Notes

Reaction equation

HRID 1157640 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([O:23][CH3:24])=[C:14]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:15]=2)[CH:5]=[CH:4][N:3]=1.[I-].[NH2:26][N+:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:10]3[CH:11]=[CH:12][C:13]([O:23][CH3:24])=[C:14]([NH:16][C:17](=[O:22])[C:18]([F:20])([F:21])[F:19])[CH:15]=3)=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=23)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 59511410N-[5-[(2-Chloro-4-pyrimidinyl)ethynyl]-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide

Product 1

HCID 59511425N-[5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamideYield 53.5%

Procedure

N-[5-[(2-Chloro-4-pyrimidinyl)ethynyl]-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide (1.7 g, 4.8 mmol) was subjected to cyclization with N-aminopyridinium iodide (2.1 g, 9.6 mmol) according to the procedure of Example 56, Step E to give the desired product (1.15 g, 53%). 1H NMR (400 MHz, d6-DMSO) δ 10.82 (s, 1H), 8.88 (d, J=6.8 Hz, 1H), 8.45 (d, J=5.6 Hz, 1H), 8.39 (d, J=8.4 Hz, 1H), 7.70 (d, J=2.0 Hz, 1H), 7.64-7.60 (m, 1H), 7.57 (dd, J=8.6 and 1.8 Hz, 1H), 7.28 (d, J=8.4 Hz, 1H), 7.21-7.18 (m, 1H), 7.11 (d, J=5.6 Hz, 1H), 3.90 (s, 3H) ppm.

Sources & evidence

ORD record
ord-d37425ba482b4fe18c0b7b2a1a423975
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…