Hydrochloric Acid → HCID 59853488, compound

HRID 2374221Notes

Reaction equation

HRID 2374221 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[C:12]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)C1C=CC=CC=1.Cl>CCO>[CH:15]([C:13]1[N:14]=[C:10]([CH2:9][OH:8])[N:11]([CH2:27][C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)[C:12]=1[S:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59853489HCID 59853489, compound

Product 1

HCID 59853488HCID 59853488, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of amine 37 (101 mg, 0.220 mmol) in EtOH (5 mL) was added conc. HCl (5 mL). See Scheme 22 (FIG. 24). After the reaction mixture was warmed to 80° C. and stirred for 16 h, the mixture was concentrated under reduced pressure and partitioned between EtOAc and sat. NaHCO3. The organic phase was dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude product was chromatographed on silica gel (eluting 5-7% MeOH/CH2Cl2) to give [4-isopropyl-5-(3-methoxy-phenylsulfanyl)-1-pyridin-4-ylmethyl-1H-imidazol-2-yl]-methanol 38 (71 mg, 87%) as a pale yellow oil.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. custompartitioned between EtOAc and sat. NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude product was chromatographed on silica gel (eluting 5-7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1288f02e70134c24bb6fe8b68b5093c0
Source dataset
uspto-grants-2008_12
Patent number
US07462608B2

Reaction notes

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