Methylamine → Regadenoson

HRID 2421465Notes

Reaction equation

HRID 2421465 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-251513cef386418ca0b266587d1abbac
Source dataset
uspto-grants-2011_06
Patent number
US07956179B2

Reaction notes

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