Hydrochloric Acid → HCID 89933055, compound

HRID 2207753Notes

Reaction equation

HRID 2207753 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:8]2=[N:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=[C:7]2[NH:6][C:5]=1[C:15]([OH:17])=O.[CH:18]([N:21](C(C)C)CC)(C)C.[C:27]([O:30]C(=O)C)(=O)[CH3:28].[OH-].[Na+].Cl>C(OCC)C.O1CCCC1>[C:27]([NH:1][CH2:2][CH2:3][C:4]1[C:8]2=[N:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=[C:7]2[NH:6][C:5]=1[C:15]([NH:21][CH3:18])=[O:17])(=[O:30])[CH3:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 118071682HCID 118071682, compound

Product 1

HCID 89933055HCID 89933055, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(2-aminoethyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (123 mg) and tetrahydrofuran (2.00 mL) were added diisopropylethylamine (0.448 mL) and acetic anhydride (0.074 mL), followed by stirring at room temperature overnight. To the mixture was added a 1 M aqueous sodium hydroxide solution (3.00 mL), followed by stirring for 1 hour, and then 1 M hydrochloric acid (3.00 mL) was added thereto, followed by concentrating under reduced pressure. The residue was suspended in ethanol, the insoluble materials were separated by filtration, and then the filtrate was concentrated under reduced pressure. To a mixture of the obtained residue (144 mg), methylamine hydrochloride (175 mg), diisopropylethylamine (0.622 mL), and N,N-dimethyl formamide (4.65 mL) was added 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (592 mg), followed by stirring at room temperature overnight. To the mixture was added water, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1 to 20:1) and the obtained crude product was solidified with diethyl ether and the obtained solid was collected by filtration and dried under reduced pressure to obtain 3-(2-acetamidoethyl)-5-methoxy-N-methyl-1H-pyrrolo[3,2-b]pyridine-2-carboxamide (81.0 mg) as a pale yellow solid.

Workup

  1. stirringby stirring for 1 hour
  2. concentrationby concentrating under reduced pressure
  3. customthe insoluble materials were separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo a mixture of the obtained residue (144 mg), methylamine hydrochloride (175 mg), diisopropylethylamine (0.622 mL), and N,N-dimethyl formamide (4.65 mL)
  6. additionwas added 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (592 mg)
  7. stirringby stirring at room temperature overnight
  8. additionTo the mixture was added water
  9. extractionfollowed by extraction with ethyl acetate
  10. washthe organic layer was washed with saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe insoluble materials were separated by filtration
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1 to 20:1)
  15. customthe obtained crude product
  16. filtrationthe obtained solid was collected by filtration
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-75f3a3142b5a49b78c072c1ac7ce1f17
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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