HCID 178432061, compound → HCID 178432060, compound

HRID 1384297Notes

Reaction equation

HRID 1384297 reaction equation
[Si]([O:8][CH:9]1[C:19]2[C:14](=[N:15][C:16]([CH3:26])=[C:17]([C:20]([NH:22][C:23]([NH2:25])=[NH:24])=[O:21])[CH:18]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1)(C(C)(C)C)(C)C>CO.Cl>[OH:8][CH:9]1[C:19]2[C:14](=[N:15][C:16]([CH3:26])=[C:17]([C:20]([NH:22][C:23]([NH2:25])=[NH:24])=[O:21])[CH:18]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 178432061HCID 178432061, compound

Product 1

HCID 178432060HCID 178432060, compoundYield 135%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

5-tert-Butyldirnethylsilyloxy-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonylguanidine (252.5 mg, 0.37 mmol) was dissolved in 5% hydrochloric acid methanol solution (10.1 ml) at 0° C. and stirred at room temperature for 14 hours. The solvent was evaporated under reduced pressure, and the thus obtained residue was mixed with chloroform:methanol (4:1), adjusted to pH 9 to 10 with 5% sodium hydroxide aqueous solution and then extracted with chloroform:methanol (4:1). The thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was crystallized from chloroform-ether to obtain the title compound (131.0 mg, 74.9%) as white powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe thus obtained residue was mixed with chloroform:methanol (4:1)
  3. extractionextracted with chloroform:methanol (4:1)
  4. washThe thus obtained organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was crystallized from chloroform-ether

Sources & evidence

ORD record
ord-d519bb050b06479889ca1a718980a379
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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