3-Amino-1-propanol → N-(3-hydroxy-propyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide

HRID 1969999Notes

Reaction equation

HRID 1969999 reaction equation
[O:1]=[C:2]1[C:11]2[NH:12][CH:13]=[C:14]([C:15]([OH:17])=O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[OH:18][CH2:19][CH2:20][CH2:21][NH2:22]>>[OH:18][CH2:19][CH2:20][CH2:21][NH:22][C:15]([C:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[NH:3][C:2](=[O:1])[C:11]=2[NH:12][CH:13]=1)=[O:17]

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 120650844-oxo-3H,4H,5H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 15605164N-(3-hydroxy-propyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamideYield 9%

Procedure

This compound is prepared according to synthesis 79 from 75 mg (0.33 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 75) and 28 μL (0.36 mmol) of 3-hydroxy-propylamine. The aqueous phase is evaporated, the residue is taken up in methanol and then filtered. The filtrate is evaporated and the residue is purified by preparative LCMS to give 8 mg (9%) of N-(3-hydroxy-propyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide in the form of a white solid.

Workup

  1. customThis compound is prepared
  2. customThe aqueous phase is evaporated
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue is purified by preparative LCMS

Sources & evidence

ORD record
ord-1ffa7500193b466282d84e27164ed6c8
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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