Ammonium Hydroxide → HCID 15521231, compound

HRID 325108Notes

Reaction equation

HRID 325108 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=2)=[CH:4][CH:3]=1.[OH-:30].[NH4+]>O.C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([S:19]([CH3:20])=[O:30])[N:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 15521230HCID 15521230, compound

Product 1

HCID 15521231HCID 15521231, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of K2S2O8 (0.20 g, 0.73 mmol) in water (5 mL) was added to 4-(4-fluorophenyl)-5-[2-(methylthio)-4-pyrimidinyl]-1-[3-(4-morpholinyl)propyl]imidazole (0.20 g, 0.48 mmol) in glacial acetic acid (10 mL). After stirring at ambient temperature for 72 h, the reaction mixture was poured into water, neutralized with concentrated aqueous ammonium hydroxide and extracted four times with dichloromethane. The organic phases were combined and evaporated. The residue was purified by flash chromatography eluting successively with 1%, 2%, 4% and 10% methanol in dichloromethane to afford the title compound as a clear oil (0.15 g, 73%). 1H NMR (CDC13) δ 8.57(d, J=7 Hz, 1H), 7.77(s,1H), 7.47 (dd, 2H), 7.18(d, J=5 Hz, 1H) 7.09(t, J=9 Hz, 2H), 4.56(m, 2H), 3.72(t, J=5 Hz, 4H), 3.00(s, 3H), 2.40(brd. s, 4H), 2.33(t, J=8 Hz, 2H), 1.94(m, 2H).

Workup

  1. extractionextracted four times with dichloromethane
  2. customevaporated
  3. customThe residue was purified by flash chromatography
  4. washeluting successively with 1%, 2%, 4% and 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-7cb7187b8e8f46a99e09538af7b1b64f
Source dataset
uspto-grants-2001_04
Patent number
US06222036B1

Reaction notes

Loading…