Potassium Carbonate → tert-butyl (1S,2R)-2-(3-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-4-cyanophenylamino)cyclohexylcarbamate

HRID 84797

반응식

HRID 84797 반응식
Br[C:2]1[CH:3]=[C:4]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[N:25]1[N:26]([C:30]2[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=2)[NH2:33])[N:27]=[CH:28][CH:29]=1.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.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:25]1[N:26]([C:30]2[CH:31]=[C:32]([NH:33][C:2]3[CH:3]=[C:4]([NH:10][C@@H:11]4[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]4[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=[CH:6][C:7]=3[C:8]#[N:9])[CH:34]=[CH:35][CH:36]=2)[N:27]=[CH:28][CH:29]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 234387563-(2H-1,2,3-Triazol-2-yl)anilineHCID 69283621tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate

생성물 1

HCID 69284027tert-butyl (1S,2R)-2-(3-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-4-cyanophenylamino)cyclohexylcarbamate

시약·촉매·용매 2

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

실험 절차

A mixture of tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate (150 mg, 0.380 mmol), 3-(2H-1,2,3-triazol-2-yl)aniline (100 mg, 0.625 mmol), BINAP (40 mg, 0.064 mmol), Pd(OAc)2 (25 mg, 0.11 mmol) and K2CO3 (150 mg, 1.08 mmol) in dioxane (3 mL) was degassed with Ar, then was stirred at 100 C for 4 h. EtOAc and water were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give tert-butyl (1S,2R)-2-(3-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-4-cyanophenylamino)cyclohexylcarbamate as a crude residue.

후처리

  1. customwas degassed with Ar
  2. additionEtOAc and water were added
  3. customThe organic phase was separated
  4. washwashed with 1N HCl
  5. dry with materialwith 5% NaHCO3, dried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3880bfdab573446e805326443415ea25
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846928B2

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