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Potassium Carbonate → tert-butyl (1S,2R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)cyclohexylcarbamate

HRID 2200423
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HRID 2200423 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:5]=[N:4][C:3]=1[C:23]#[N:24].[NH2:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:23]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][C:2]=1[NH:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1)#[N:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 133964-AminobenzonitrileHCID 634876Binap, (A+-)-HCID 86685544tert-butyl (1S,2R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate

생성물 1

HCID 86685553tert-butyl (1S,2R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)cyclohexylcarbamate수율 149.6%

시약·촉매·용매

2
HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of tert-butyl (1S,2R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate (90 mg, 0.256 mmol), 4-aminobenzonitrile (42 mg, 0.355 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. Water and EtOAc were added. Organic phase was separated, dried over Na2SO4, concentrated in vacuo to give a crude tert-butyl (1S,2R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)cyclohexylcarbamate (166 mg).

후처리

  1. customwas degassed with Ar
  2. additionWater and EtOAc were added
  3. customOrganic phase was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2a9edf7195d0423c81ce295bd4767e1f
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359308B2

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