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Triethylamine → N-(6-(5-cyanopyrazin-2-ylamino)-4-(1-Boc-piperidin-4-ylmethylamino)pyridin-3-yl)ethanesulfonamide

HRID 384634
ノート
印刷プレビュー

反応式

HRID 384634 の反応式
C(N(CC)CC)C.[CH2:8]([S:10](Cl)(=[O:12])=[O:11])[CH3:9].[NH2:14][C:15]1[C:16]([NH:30][CH2:31][CH:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]2)=[CH:17][C:18]([NH:21][C:22]2[CH:27]=[N:26][C:25]([C:28]#[N:29])=[CH:24][N:23]=2)=[N:19][CH:20]=1>CN(C=O)C>[C:28]([C:25]1[N:26]=[CH:27][C:22]([NH:21][C:18]2[N:19]=[CH:20][C:15]([NH:14][S:10]([CH2:8][CH3:9])(=[O:12])=[O:11])=[C:16]([NH:30][CH2:31][CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)[CH:17]=2)=[N:23][CH:24]=1)#[N:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 11667Ethanesulfonyl chloride2 回HCID 59613544Tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

生成物 1

HCID 66745434N-(6-(5-cyanopyrazin-2-ylamino)-4-(1-Boc-piperidin-4-ylmethylamino)pyridin-3-yl)ethanesulfonamide

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

Triethylamine (15 μL, 0.11 mmol) and ethylsulfonylchloride (8 μL, 0.78 mmol) were added to a stirred solution of tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)-pyridin-4-ylamino)-methyl)-piperidine-1-carboxylate (30.3 mg, 0.071 mmol) in DMF (1 mL) at 0° C. After 1.5 hours at room temperature, further ethylsulfonylchloride (5.5 μL, 0.53 mmol) and triethylamine (7.5 μL, 0.53 mmol) were added. After 1 hour the reaction mixture was partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane. The combined organic phases were dried (Na2SO4) and concentrated. Preparative HPLC gave N-(6-(5-cyanopyrazin-2-ylamino)-4-(1-Boc-piperidin-4-ylmethylamino)pyridin-3-yl)ethanesulfonamide as a solid. The material was dissolved in 20% trifluoroacetic acid in dichloromethane. After 20 minutes the mixture was loaded onto a MP-TsOH SPE cartridge and eluted with 2M ammonia in methanol. The basic fractions were combined to give N-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-4-ylmethylamino)pyridin-3-yl)ethanesulfonamide (2.28 mg, 8%).

後処理

  1. customAfter 1 hour the reaction mixture was partitioned between dichloromethane and water
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-c8e4c15b75144b76b151f96de163846a
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367658B2

反応ノート

読み込み中…

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