Sulfuric Acid → HCID 59160544, compound

HRID 1958667Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:15]=2)=[CH:6][C:3]=1[C:4]#N.[OH:33]S(O)(=O)=O.[OH-:38].[Na+]>O>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:15]=2)=[CH:6][C:3]=1[C:4]([OH:33])=[O:38]

Participants

Conditions

Temperature: 120 °C

Procedure

2-Fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzonitrile (Example 76) (300 mg, 0.715 mmol) was treated with conc. H2SO4 (2.4 mL) and H2O (0.8 ml) and the mixture was stirred at 120° C. for 10 hours. The reaction mixture was cooled to room temperature and basified to pH 9-10 with 5N NaOH solution in the ice bath. The solution was extracted with CH2Cl2 (5 mL, 3 times), and then the aqueous layer was acidified to pH 4 with 2N HCl solution. The precipitate was filtered, washed with H2O, and dried under vacuum for overnight to afford the title compound (213 mg, 49%). (300 MHz, CDCl3+CD3OD) δ 2.48 (3H, s), 4.15 (2H, s), 6.97 (1H, d), 7.05 (1H, dd), 7.14 (1H, d), 7.35-7.42 (2H, m), 7.47-7.52 (1H, m), 7.83 (1H, dd), 7.90 (1H, dd), 8.01 (1H, d), 8.08 (1H, d), 8.16 (1H, dd), 8.80 (1H, dd). MS (ESI) m/z 439 (MH+).

Workup

extractionThe solution was extracted with CH2Cl2 (5 mL, 3 times)
filtrationThe precipitate was filtered
washwashed with H2O
customdried under vacuum for overnight

Sources & evidence

ORD record: ord-206986b127174f7288f5a84c9ae60887
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410146B2

Reaction notes

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