Ammonium Acetate → HCID 21913208, compound

HRID 1245967Notes

Reaction equation

[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:15]([CH3:17])=[C:14]([CH3:18])[N:13]=[C:12](OC3C=CC=CC=3)[C:11]=2[N:10]=[C:9]1[CH2:26][CH2:27][CH3:28])(=[O:4])=[O:3].C([O-])(=O)C.[NH4+:33]>>[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:15]([CH3:17])=[C:14]([CH3:18])[N:13]=[C:12]([NH2:33])[C:11]=2[N:10]=[C:9]1[CH2:26][CH2:27][CH3:28])(=[O:4])=[O:3]

Participants

Reactant 2

HCID 517165Ammonium Acetate

HCID 21913594HCID 21913594, compound

Product 1

HCID 21913208HCID 21913208, compoundYield 67.2%

Procedure

Using the general method of Example 89 Part H, 1-[3-(methanesulfonyl)propyl]-6,7-dimethyl-4-phenoxy-2-propyl-1H-imidazo[4,5-c]pyridine (2.1 g, 5.23 mmol) was reacted with ammonium acetate (25 g) and purified to provide 1.14 g of 1-[3-(methanesulfonyl)propyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine as white needles, mp 153.5–155.0° C. 1H NMR (300 MHz, CDCl3) δ 4.83 (br s, 2H), 4.48–4.42 (m, 2H), 3.07 (t, J=7.1 Hz, 2H), 2.95 (s, 3H), 2.82–2.77 (m, 2H), 2.45 (s, 6H), 2.35–2.25 (m, 2H), 1.94–1.81 (m, 2H), 1.07 (t, J=7.3 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 153.2, 148.3, 147.1, 138.9, 125.4, 104.0, 51.2, 42.9, 41.3, 29.5, 24.3, 22.1, 21.5, 14.0, 13.1;

Workup

custompurified

Sources & evidence

ORD record: ord-f616183f95c34becbe7deef29b36127f
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125890B2

Reaction notes

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