Hydrochloric Acid → HCID 178494612, compound

HRID 1836304Notes

Reaction equation

HRID 1836304 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9]([CH:11]([O:22][CH3:23])[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[N:8]=[C:7]1[Si](C(C)(C)C)(C)C)(=O)=O.Cl>>[NH:6]1[CH:10]=[C:9]([CH:11]([O:22][CH3:23])[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[N:8]=[CH:7]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 53745957HCID 53745957, compound

Product 1

HCID 178494612HCID 178494612, compoundYield 100%

Procedure

To 2-(tert-Butyldimethylsilyl)-4-(methoxyquinolin-4-yl-methyl)-imidazole-1-sulfonic acid dimethylamide. (0.32 g, 0.672 mmol), 7 ml of 1.5N HCl was added and the solution refluxed for two hours. The reaction mixture was concentrated, partitioned between water(10 ml) and EtOAc (2×10 ml). The organic layer was dried over sodium sulfate, filtered, concentrated and column purified (CH2Cl2: MeOH: methanol-NH-2 (1.0 M); (4.5:0.25:0.25) to yield 0.160 g (100%) of the product as a syrup.

Workup

  1. temperaturethe solution refluxed for two hours
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between water(10 ml) and EtOAc (2×10 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customcolumn purified (CH2Cl2

Sources & evidence

ORD record
ord-38ba90a336c843e788860473502e33d6
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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