Methanol → HCID 67314150, compound

HRID 1011590Notes

Reaction equation

HRID 1011590 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][CH2:22][N:23](CC2C=CC=CC=2)[CH3:24])=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].CO>[Pd].CN(C)C=O>[ClH:19].[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:20][CH2:21][CH2:22][NH:23][CH3:24])=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 59285815HCID 59285815, compound

Product 1

HCID 67314150HCID 67314150, compoundYield 110.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium on activated carbon (10 mg) was added to a solution of 2-aminocarbonylamino-5-[2-[2-(N-benzyl-N-methylamino)ethyloxy]-5-chlorophenyl]pyrrole-3-carboxamide (Compound No. 8-21, 26 mg, 0.059 mmol) in the mixed solvent (methanol:N,N-dimethylformamide=10:1, 2.2 mL) and the mixture was stirred at room temperature for 2.5 hours under hydrogen gas atmosphere. After the reaction solution was filtered, the filtrate was concentrated in vacuo. The obtained solid was washed with a mixed solvent (6 mL), which consists of chloroform and diethyl ether (1:1), and dried under reduced pressure to give the target compound (23 mg) quantitatively as a colorless solid.

Workup

  1. filtrationAfter the reaction solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThe obtained solid was washed with a mixed solvent (6 mL), which
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-027d81f848db43ceb047a7f34e1352ae
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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