1-Butanol → HCID 178450353, compound

HRID 1728587Notes

Reaction equation

HRID 1728587 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].C([CH:14]1[N:26]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[NH:44][N:43]=[N:42][N:41]=3)=[CH:30][CH:29]=2)[C:17]2=[N:18][C:19](=S(=O)=O)[CH:20]=[C:21]([CH3:22])[C:16]2=[N:15]1)C.Cl>O.CN(C=O)C>[CH2:1]([O:5][C:14]1[N:26]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[NH:44][N:43]=[N:42][N:41]=3)=[CH:32][CH:33]=2)[C:17]2=[N:18][CH:19]=[CH:20][C:21]([CH3:22])=[C:16]2[N:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 178437465HCID 178437465, compound

Product 1

HCID 178450353HCID 178450353, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 100 mg (1.3 mmol) of n-butanol, 400 mg (3.6 retool) of potassium tert.-butoxide and DMF was heated at 80 degree C for 5 minutes. 300 mg (0.65 mmol) of 2-ethyl-sulfonyl-7-methyl-3[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-3H-imidazo[4.5-b]pyridine was added to the mixture. The resultant was heated for 2 hours. The reaction product mixture was mixed with water, neutralized with 2n HCl and extracted with dichloromethane. The dichloromethane phase was washed with a saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled out at a reduced pressure and the residue was treated with ether-hexane-dichloromethane or re-crystallization to obtained 140 mg of the intended compound.

Workup

  1. temperaturewas heated at 80 degree C for 5 minutes
  2. temperatureThe resultant was heated for 2 hours
  3. extractionextracted with dichloromethane
  4. washThe dichloromethane phase was washed with a saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled out at a reduced pressure
  7. additionthe residue was treated with ether-hexane-dichloromethane or re-crystallization

Sources & evidence

ORD record
ord-7858d5781a9747a180a8754d2d22ed90
Source dataset
uspto-grants-1994_07
Patent number
US05328911

Reaction notes

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