Methylamine → Regadenoson

HRID 60619

反応式

HRID 60619 の反応式
CO[C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[N:11]=[C:12]([NH2:28])[C:13]3[N:14]=[CH:15][N:16]([C:26]=3[N:27]=2)[C@@H:17]2[O:25][C@H:22]([CH2:23][OH:24])[C@@H:20]([OH:21])[C@H:18]2[OH:19])[CH:9]=1)=[O:4].[CH3:29][NH2:30]>CO>[CH3:29][NH:30][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[N:11]=[C:12]([NH2:28])[C:13]3[N:14]=[CH:15][N:16]([C:26]=3[N:27]=2)[C@@H:17]2[O:25][C@H:22]([CH2:23][OH:24])[C@@H:20]([OH:21])[C@H:18]2[OH:19])[CH:9]=1)=[O:4]

参加物

4

反応物 2

HCID 6329MethylamineHCID 71270364Regadenoson Impurity 3

生成物 1

HCID 219024Regadenoson

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
20 °C

実験手順

A suspension of 1 g of 2-(4-methoxycarbonylpyrazol-1-yl)adenosine in 10 ml of 40% methylamine in methanol is stirred in a closed flask at 20° C. until formation of a solution (3 to 5 hours). The produced solution is left to stand at the given temperature for additional 15 hours. The solution is then filtered with active charcoal and the filtrate is concentrated in vacuo. The evaporation residue, which is the amorphous form of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine, is dissolved in 2 ml of dimethylsulfoxide and left to cool down freely to room temperature. The resulting turbid solution is added to 20 ml of methanol. The separated gel-like precipitate is stirred under the boil for 1.5-2.5 hours, wherein a powder-like suspension is formed. After cooling down, sucking off, and drying, 0.8 g of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine polymorph E is obtained.

後処理

  1. waitThe produced solution is left
  2. waitto stand at the given temperature for additional 15 hours
  3. filtrationThe solution is then filtered with active charcoal
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionis dissolved in 2 ml of dimethylsulfoxide
  6. waitleft
  7. temperatureto cool down freely to room temperature
  8. additionThe resulting turbid solution is added to 20 ml of methanol
  9. stirringThe separated gel-like precipitate is stirred under the boil for 1.5-2.5 hours
  10. customwherein a powder-like suspension is formed
  11. temperatureAfter cooling down
  12. customdrying

出典と根拠

ORDレコード
ord-5bff3236154745458a05360125466024
出典データセット
uspto-grants-2016_09
特許番号
US09441006B2

関連ノート

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