Tetrahydrofurfuryl alcohol → HCID 25003273, compound

HRID 1011588Notes

Reaction equation

HRID 1011588 reaction equation
[BH4-].[Na+].[NH2:3][C:4]([NH:6][C:7]1[NH:8][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[C:10]([CH:15]=[O:16])[C:11]=1[C:12]([NH2:14])=[O:13])=[O:5].O1CCCC1CO>[Cl-].[NH4+]>[NH2:3][C:4]([NH:6][C:7]1[NH:8][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[C:10]([CH2:15][OH:16])[C:11]=1[C:12]([NH2:14])=[O:13])=[O:5]

Participants

5

Reactant 3

HCID 7360Tetrahydrofurfuryl alcoholHCID 4311764Sodium borohydrideHCID 25003272HCID 25003272, compound

Product 1

HCID 25003273HCID 25003273, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

Sodium borohydride (18 mg, 0.48 mmol) was added to a solution of 2-aminocarbonylamino-5-(3-chlorophenyl)-4-formylpyrrole-3-carboxamide (Compound No. 17-1, 50 mg, 0.16 mmol) in the mixed solvent (tetrahydrofuran methanol=2:1, 1.5 mL) and the mixture was stirred at room temperature for 4 hours. Saturated aqueous ammonium chloride solution (50 mL) was added to the reaction solution, extracted with ethyl acetate (50 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained solid was washed with chloroform (15 mL) and dried under reduced pressure to give the target compound (19 mg) as an orange solid (Yield 37%).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. washThe obtained solid was washed with chloroform (15 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8d8e384063eb4b13aecec554da2a1688
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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