Sodium methanethiolate → HCID 59285893, compound

HRID 1011585Notes

Reaction equation

HRID 1011585 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].[CH3:21][S-:22].[Na+]>FC(F)(F)C(O)=O.ClCCl>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][S:22][CH3:21])[CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 59285923HCID 59285923, compound

Product 1

HCID 59285893HCID 59285893, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Under a solution of 2-aminocarbonylamino-5-(3-formylphenyl)pyrrole-3-carboxamide (Compound No. 14-2, 50 mg, 0.18 mmol) in trifluoroacetic acid (4 mL) was added to a solution of sodium methanethiolate (14 mg, 0.20 mmol) in dichloromethane (2 mL) and the mixture was stirred for 10 minutes. Moreover, borane-pyridine complex (41 μL, 0.41 mmol) was added thereto and the whole was stirred for 10 minutes. The reaction solution was concentrated in vacuo. Saturated aqueous sodium hydrogencarbonate (3 mL) and water (2 mL) were added to the residue, extracted with ethyl acetate (10 mL). After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the target compound (22 mg) as a colorless solid (Yield 39%).

Workup

  1. additionMoreover, borane-pyridine complex (41 μL, 0.41 mmol) was added
  2. stirringthe whole was stirred for 10 minutes
  3. concentrationThe reaction solution was concentrated in vacuo
  4. additionSaturated aqueous sodium hydrogencarbonate (3 mL) and water (2 mL) were added to the residue
  5. extractionextracted with ethyl acetate (10 mL)
  6. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-37d58aa220c94596a572f904d7139d68
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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