Hydrochloric Acid → HCID 178432943, compound

HRID 1498785Notes

Reaction equation

HRID 1498785 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12](S(C)(=O)=O)[N:11]=[C:10]([C@@H:18]3[CH2:20][C@H:19]3[C:21]3[N:25]([CH3:26])[C:24]4[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=4[N:22]=3)[CH:9]=2)[N:3]=1.[OH-:31].[Na+].O.Cl>O1CCOCC1>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:9]=[C:10]([C@@H:18]3[CH2:20][C@H:19]3[C:21]3[N:25]([CH3:26])[C:24]4[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=4[N:22]=3)[N:11]=[C:12]([OH:31])[N:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86732046HCID 86732046, compound

Product 1

HCID 178432943HCID 178432943, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of trans-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(methylsulfonyl)pyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (1-6, 33.0 mg, 0.077 mmol, 1.0 eq.) in 1,4-dioxane (0.8 mL) was added 2 M NaOH in H2O (0.39 mL, 0.78 mmol, 10 eq.), and the resulting mixture was stirred at ambient temperature for 1 hour. The reaction mixture was neutralized by the addition of aqueous concentrated HCl and the resulting precipitate was filtered, washed with 1,4-dioxane (2.0 mL) and dried to afford trans-4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl)pyrimidin-2-ol (20) as an amorphous white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.2 (br s, 1H), 7.54 (br d, 11-1, J=7.5 Hz), 7.51 (br d, 1H, J=7.5 Hz), 7.22 (br t, 1H, J=7.5 Hz), 7.17 (br t, 1H, J=7.5 Hz), 6.73 (br s, 1H), 3.85 (s, 3H), 3.04 (m, 1H), 2.76 (s, 3H), 2.64 (m, 1H), 2.30 (s, 3H), 1.94-1.80 (m, 2H). LRMS m/z (M+H) 362 found, 362 required.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with 1,4-dioxane (2.0 mL)
  3. customdried

Sources & evidence

ORD record
ord-4a8313b593a3419bb86fe33fa8eb5cad
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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