Sodium Hydroxide → HCID 56675696, compound

HRID 2220458Notes

Reaction equation

HRID 2220458 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:22]2[CH:26]=[C:25]([C:27]3([CH2:32][CH3:33])OCC[O:28]3)[S:24][CH:23]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[C:16]([F:21])=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)[N:3]=1.[OH-].[Na+]>C(OCC)C.Cl.C(Cl)Cl>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[C:16]([F:21])=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)([C:22]2[CH:26]=[C:25]([C:27](=[O:28])[CH2:32][CH3:33])[S:24][CH:23]=2)[N:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59772739HCID 59772739, compound

Product 1

HCID 56675696HCID 56675696, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-amino-5-[5-(2-ethyl-[1,3]dioxolan-2-yl)-thiophen-3-yl]-5-[3-(2-fluoro-pyridin-3-yl)-phenyl]-3-methyl-3,5-dihydro-imidazol-4-one (0.11 g, 0.23 mmol) in diethyl ether and 1 N HCl was heated at reflux temperature for 1 h, cooled to room temperature, diluted with methylene chloride and basified to pH 9 using 2 N sodium hydroxide. The phases were separated. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resultant concentrate was freeze dried from 1:1 acetonitrile/water (4 mL) to afford the title compound as a white solid, 0.069 g (71% yield), mp 98-112° C.; 1H NMR (500 MHz, CDCl3) δ 8.19 (dt, J=4.7, 1.4 Hz, 1H), 7.85-7.81 (m, 1H), 7.78-7.69 (m, 3H), 7.61-7.55 (m, 1H), 7.52-7.48 (m, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.29-7.23 (m, 1H), 3.12 (s, 3H), 2.88 (q, J=7.3 Hz, 2H), 1.17 (t, J=7.3 Hz, 3H); ESI MS m/z 423 [C22H19FN4O2S+H].

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. customThe phases were separated
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. concentrationThe resultant concentrate
  8. dry with materialdried from 1:1 acetonitrile/water (4 mL)

Sources & evidence

ORD record
ord-c007c962b5ed47c5935be85e3b439ee3
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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