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

HRID 384634
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HRID 384634 반응식
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]
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참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 11667Ethanesulfonyl chloride2회HCID 59613544Tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c8e4c15b75144b76b151f96de163846a
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367658B2

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