HCID 58692573, compound → HCID 11524049, compound

HRID 423231Notes

Reaction equation

HRID 423231 reaction equation
[C:1]([C:5]1[CH:29]=[CH:28][C:8]([C:9]([NH:11][C:12]2[C:13]([O:26]C)=[N:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=3)[CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[C:13](=[O:26])[NH:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=3)[CH:17]=2)=[O:10])=[CH:28][CH:29]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58692573HCID 58692573, compound

Product 1

HCID 11524049HCID 11524049, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

4-tert-Butyl-N-[2-methoxy-5-(2-methylsulfanyl-pyrimidin-4-yl)-pyridin-3-yl]-benzamide (120 mg, 0.29 mmol) was dissolved in 1,4-dioxane (6 mL) and water (1.2 mL). Concentrated Hcl (600 μL) was added and the reaction mixture was heated to reflux for 30 minutes. The reaction mixture was cooled down to room temperature and water was added. The obtained precipitate was isolated by filtration and dried under vacuum. The crude solid was purified by flash chromatography to give the title compound as a fawn solid (29 mg, 25% yield). MS (ES+) m/e=395. 1H NMR (DMSO-d6) δH 1.33 (9H, s), 2.58 (3H, s), 7.59 (2H, d), 7.64 (1H, d), 7.88 (2H, d), 8.21 (1H, s), 8.58 (1H, d), 9.11 (1H, s), 9.30 (1H, s), 12.72 (1H, br s).

Workup

  1. additionConcentrated Hcl (600 μL) was added
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 30 minutes
  4. customThe obtained precipitate was isolated by filtration
  5. customdried under vacuum
  6. customThe crude solid was purified by flash chromatography

Sources & evidence

ORD record
ord-4649985dfa7848dba0f4d96154efb2e4
Source dataset
uspto-grants-2012_01
Patent number
US08101770B2

Reaction notes

Loading…