Acetic Acid → (R)-5-(1-amino-3-cyclopropyl-1-oxopropan-2-ylamino)-3-(thieno[2,3-b]pyridin-3-ylamino)pyrazine-2-carboxamide

HRID 2200412ノート

反応式

HRID 2200412 の反応式
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:19][C@H:20]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:21]([NH2:23])=[O:22])=[N:7][C:8]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[S:12][CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:34]>CCO.CS(C)=O>[NH2:23][C:21](=[O:22])[C@H:20]([NH:19][C:6]1[N:7]=[C:8]([NH:9][C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[S:12][CH:11]=2)[C:3]([C:1]([NH2:2])=[O:34])=[N:4][CH:5]=1)[CH2:24][CH:25]1[CH2:26][CH2:27]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685543(R)-2-(5-cyano-6-(thieno[2,3-b]pyridin-3-ylamino)pyrazin-2-ylamino)-3-cyclopropylpropanamide

生成物 1

HCID 71573436(R)-5-(1-amino-3-cyclopropyl-1-oxopropan-2-ylamino)-3-(thieno[2,3-b]pyridin-3-ylamino)pyrazine-2-carboxamide

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 702Ethanol溶媒

実験手順

The compound (R)-2-(5-cyano-6-(thieno[2,3-b]pyridin-3-ylamino)pyrazin-2-ylamino)-3-cyclopropylpropanamide (33 mg, 0.087 mmol) was dissolved in EtOH (2 mL) and DMSO (1 mL), aq. 1N NaOH (1.0 mL) and aq. H2O2 (30%, 1.0 mL) were added. The mixture was stirred at room temperature for 30 min. HOAc (0.5 mL) was added. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (34 mg). MS 398.2 (M+H); UV 203.6, 224.8, 262.1, 294.1, 357.3 nm; t 0.532 min.

後処理

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe residue was purified by HPLC

出典と根拠

ORDレコード
ord-2bbe71abe6e64c1ebe7eadec1b971609
出典データセット
uspto-grants-2016_06
特許番号
US09359308B2

反応ノート

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