m-Toluidine → tert-butyl (1S,2R)-2-(4-cyano-3-(m-tolylamino)phenylamino)cyclohexylcarbamate

HRID 84792

반응식

HRID 84792 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].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=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.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]([C:7]1[CH:6]=[CH:5][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:3][C:2]=1[NH:25][C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1)#[N:9]

참가 물질

7

반응물 4

HCID 7934m-ToluidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 69283621tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate

생성물 1

HCID 69284029tert-butyl (1S,2R)-2-(4-cyano-3-(m-tolylamino)phenylamino)cyclohexylcarbamate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

A mixture of tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate (98 mg, 0.25 mmol), m-toluidine (54 uL, 0.50 mmol), BINAP (31 mg, 0.050 mmol), Pd(OAc)2 (12 mg, 0.053 mmol) and Cs2CO3 (160 mg, 0.49 mmol) in toluene (3 mL) was degassed with Ar, then was stirred at 100 C for 3 h. EtOAc and water were added. The organic phase was separated, washed with 1N HCl, then with brine, dried over Na2SO4, concentrated in vacuo to give tert-butyl (1S,2R)-2-(4-cyano-3-(m-tolylamino)phenylamino)cyclohexylcarbamate as a 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 brine, dried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-47449be5950b4000a5aa0d6e3bbc9d3d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846928B2

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