1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 384668노트

반응식

HRID 384668 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:21]=[C:20]([NH:22][C:23]3[CH:28]=[N:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=3)[N:19]=[CH:18][C:17]=2[N:31]2[CH:35]=[CH:34][C:33]([C:36](O)=[O:37])=[CH:32]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si:39]([O:46][CH2:47][CH2:48][NH2:49])([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].C(N(C(C)C)C(C)C)C.O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C=O)C>[Si:39]([O:46][CH2:47][CH2:48][NH:49][C:36]([C:33]1[CH:34]=[CH:35][N:31]([C:17]2[C:16]([NH:15][CH2:14][CH:10]3[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]3)=[CH:21][C:20]([NH:22][C:23]3[CH:28]=[N:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=3)=[N:19][CH:18]=2)[CH:32]=1)=[O:37])([C:42]([CH3:44])([CH3:45])[CH3:43])([CH3:41])[CH3:40]

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 667465061-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid

생성물 1

HCID 66745676tert-butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (80 mg, 0.154 mmol) was dissolved in DMF (1.5 mL). 2-(tert-Butyldimethylsilyloxy)ethanamine (41 mg, 0.230 mmol), N-ethyldiisopropylamine (30 mg, 0.230 mmol), 1-hydroxy benzotriazole hydrate (31 mg, 0.230 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (44 mg, 0.23 mmol) were added to the solution and the reaction mixture was stirred for 14 h at room temperature. The solution was partitioned between dichloromethane and water. The two phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried (Na2SO4) and evaporated to give tert-butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (80 mg, 78%) which was used in the next step without purification.

후처리

  1. customThe solution was partitioned between dichloromethane and water
  2. customThe two phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-5700995f5c1b4ced9f95486ce6ac0911
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367658B2

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