Methylamine → HCID 67145436, compound

HRID 912525Notes

Reaction equation

[C:1]([C:3]1[C:8]2[N:9]=[CH:10][N:11](C)[C:7]=2[CH:6]=[C:5]([C:13]2[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]3[N:24]=[C:23]([C:25]([O:27]C)=O)[CH:22]=[CH:21][CH:20]=3)=[C:15]([C:31]([F:34])([F:33])[F:32])[CH:14]=2)[N:4]=1)#[N:2].[CH3:35][NH2:36]>CO.O>[CH3:35][NH:36][C:25]([C:23]1[N:24]=[C:19]([CH2:18][O:17][C:16]2[CH:29]=[CH:30][C:13]([C:5]3[N:4]=[C:3]([C:1]#[N:2])[C:8]4[N:9]=[CH:10][NH:11][C:7]=4[CH:6]=3)=[CH:14][C:15]=2[C:31]([F:33])([F:32])[F:34])[CH:20]=[CH:21][CH:22]=1)=[O:27]

Participants

Conditions

Temperature: 120 °C

Procedure

The mixture of methyl 6-((4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)methyl)picolinate (0.064 mmol, 30 mg) and methylamine in methanol (2M, 1 ml) was heated with microwaves at 120° C. for 10 minutes, then diluted with water (3 ml). The product was collected by filtration and washed with cold methanol (3 ml) to give 6-(4-((6-(methylaminocarbonyl)pyridin-2-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (22 mg). 1H NMR (DMSO) δ: 8.80 (s, 1H), 8.77 (m, 1H, NH), 8.76 (s, 1H), 8.54 (m, 2H), 8.16 (m, 1H), 8.06 (d, 1H), 7.76 (d, 1H), 7.59 (d, 1H), 5.58 (s, 2H), 4.04 (s, 3H). MS m/z 467 (M+1).

Workup

filtrationThe product was collected by filtration
washwashed with cold methanol (3 ml)

Sources & evidence

ORD record: ord-6638ea60d1cc4a188da6c7082f6193ab
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026236B2

Reaction notes

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