Morpholine → tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-(morpholinomethyl)-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 556821노트

반응식

HRID 556821 반응식
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)[C:13]([N:31]3[CH:35]=[CH:34][C:33]([CH:36]=O)=[CH:32]3)=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2].[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CC(O)=O>[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)[C:13]([N:31]3[CH:35]=[CH:34][C:33]([CH2:36][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[CH:32]3)=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2]

참가 물질

6

반응물 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 86648387tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-formyl-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

생성물 1

HCID 66746356tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-(morpholinomethyl)-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매

실험 절차

Crude tert-butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-formyl-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (143 mg of 50% pure material, approx. 0.142 mmol) was dissolved in DCE (1.5 mL) and AcOH (0.15 mL). Morpholine (18.5 uL, 0.213 mmol) and sodium triacetoxyborohydride (75 mg, 0.355 mmol) were added and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned between dichloromethane and 10% aqueous NaHCO3. The two phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were evaporated to dryness and the product (90 mg) was used without further purification.

후처리

  1. customThe reaction mixture was partitioned between dichloromethane and 10% aqueous NaHCO3
  2. customThe two phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. customThe combined organic phases were evaporated to dryness
  5. customthe product (90 mg) was used without further purification

출처 및 근거

ORD 기록
ord-c1092b4dea4a4ab28e0e7e0967dac05c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058045B2

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