Methylamine → Regadenoson

HRID 2242477Notes

Reaction equation

HRID 2242477 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:20]1[CH:24]=[C:23]([C:25]([O:27]CC)=O)[CH:22]=[N:21]1)=[N:14][C:15]=2[NH2:19].[CH3:30][NH2:31]>>[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:20]1[CH:24]=[C:23]([C:25]([NH:31][CH3:30])=[O:27])[CH:22]=[N:21]1)=[N:14][C:15]=2[NH2:19]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 9865974Ethyl 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

Product 1

HCID 219024Regadenoson

Procedure

A mixture of ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate (46.4 g) and methylamine (40% in water, 600 ml) was stirred at ambient temperature for about 4 hours, following the progress of the reaction by HPLC analysis. The majority of the excess methylamine was removed under reduced pressure, and the remaining mixture cooled at 0° C. for 2 hours. The solid material was filtered off, washed with ice-cold 200 proof ethanol, and dried under reduced pressure, to provide (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazol-4-yl)-N-methylcarboxamide as its monohydrate.

Workup

  1. customthe progress of the reaction by HPLC analysis
  2. customThe majority of the excess methylamine was removed under reduced pressure
  3. temperaturethe remaining mixture cooled at 0° C. for 2 hours
  4. filtrationThe solid material was filtered off
  5. washwashed with ice-cold 200 proof ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-8057f19799d34b5e8d3b34e623d34e10
Source dataset
uspto-grants-2010_03
Patent number
US07671192B2

Reaction notes

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