Ammonia → Methanesulfonic Acid

HRID 912504Notes

Reaction equation

HRID 912504 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([C:22]#[N:23])[C:19]3[N:24]=[CH:25][N:26]([CH3:27])[C:18]=3[CH:17]=2)=[CH:12][C:11]=1[C:28]([F:31])([F:30])[F:29])(=[O:4])=[O:3].[NH3:32]>CO>[NH2:32][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([C:22]#[N:23])[C:19]3[N:24]=[CH:25][N:26]([CH3:27])[C:18]=3[CH:17]=2)=[CH:12][C:11]=1[C:28]([F:29])([F:30])[F:31].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 576575423-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate

Product 2

HCID 6395Methanesulfonic AcidHCID 594106696-[4-(3-aminopropoxy)-3-(trifluoromethyl)-phenyl]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-[4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy]propyl methanesulfonate (500 mg), and ammonia in methanol (7M, 10 ml) was heated at 120° C. under microwave conditions for 20 minutes. After removal of solvent under vacuum, the expected product 6-[4-(3-aminopropoxy)-3-(trifluoromethyl)-phenyl]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile was obtained as methanesulphonic acid salt. 1H NMR (CD3OD) δ: 8.44 (s, 1H), 8.35-8.42 (m, 3H), 7.36 (d, 1H), 4.32 (t, 2H), 4.02 (s, 3H), 3.23 (t, 2H), 2.25 (m, 2H).

Workup

  1. customAfter removal of solvent under vacuum

Sources & evidence

ORD record
ord-da61375845654e7ab6fadc4a93cd79eb
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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