Hydrochloric Acid → HCID 44193182, compound

HRID 1855430Notes

Reaction equation

HRID 1855430 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Cl[C:17]1[N:22]=[C:21]([C:23]([OH:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([O:27][CH2:28][CH3:29])[N:18]=1.Cl>C(O)C.C(OCC)(=O)C>[CH2:28]([O:27][C:19]1[N:18]=[C:17]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:22]=[C:21]([C:23]([OH:26])([CH3:25])[CH3:24])[CH:20]=1)[CH3:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 86633624HCID 86633624, compound

Product 1

HCID 44193182HCID 44193182, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (102 mg, 0.5 mmol), 2-(2-chloro-6-ethoxy-pyrimidin-4-yl)-propan-2-ol (108 mg, 0.5 mmol) and 1 N aqueous hydrochloric acid (0.025 mL) in ethanol (0.8 mL) was heated in a sealed tube in a microwave oven to 170° C. for 45 min. The mixture was cooled, diluted with ethyl acetate (50 mL), and then washed with water (20 mL) and brine (20 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residual material was purified by chromatography on silica gel using dichloromethane/0-10% ethanol as eluent to give the title compound (20 mg, 10%) as yellow foam. MS ISP (m/e): 384.3 [(M+H)+].)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.20, 7.78, 7.75 and 7.63 (4 d, 4×2H), 7.31 (s, 2H), 7.16 (s, 1H), 3.93 (s, 1H), 2.53 (s, 3H), 1.61 (s, 6H).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residual material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7849b8c7e19e435aa9c52a00f18aa1b4
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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