Ethyl Acetate → 4-Chloro-N-{2-[4-(difluoromethoxy)phenyl]ethyl}-6-methoxy-1,3,5-triazin-2-amine

HRID 517482

반응식

HRID 517482 반응식
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.CCN(C(C)C)C(C)C.[F:20][CH:21]([F:32])[O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH2:31])=[CH:25][CH:24]=1.CCOC(C)=O>C(#N)C.O>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]=[C:2]([NH:31][CH2:30][CH2:29][C:26]2[CH:25]=[CH:24][C:23]([O:22][CH:21]([F:20])[F:32])=[CH:28][CH:27]=2)[N:7]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 192672,4-Dichloro-6-methoxy-3,5-triazineHCID 81531DiisopropylethylamineHCID 49622922-(4-(Difluoromethoxy)phenyl)ethan-1-amine

생성물 1

HCID 896197934-Chloro-N-{2-[4-(difluoromethoxy)phenyl]ethyl}-6-methoxy-1,3,5-triazin-2-amine수율 31.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A solution of 1.8 g of 2,4-dichloro-6-methoxy-1,3,5-triazine in 40 ml of acetonitrile is cooled on an ice bath, 1.28 ml of DIPEA and then 1.68 g of 2-[4-(difluoromethoxy)phenyl]ethanamine are added and the mixture is stirred for 30 minutes. The reaction mixture is diluted by adding 100 ml of EtOAc and 50 ml of water, the phases are separated by settling, the organic phase is washed with saturated NaCl solution and dried over MgSO4, and the solvent is evaporated off under vacuum. The residue is taken up in DCM, the insoluble matter is filtered off and the filtrate is concentrated under vacuum. The residue is chromatographed on silica gel, eluting with a cyclohexane/EtOAc mixture in a gradient of from (95/5 v/v) to (80/20 v/v). 0.94 g of the expected compound is obtained.

후처리

  1. additionThe reaction mixture is diluted
  2. customthe phases are separated
  3. washthe organic phase is washed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. filtrationthe insoluble matter is filtered off
  7. concentrationthe filtrate is concentrated under vacuum
  8. customThe residue is chromatographed on silica gel
  9. washeluting with a cyclohexane/EtOAc mixture in a gradient of from (95/5 v/v) to (80/20 v/v)

출처 및 근거

ORD 기록
ord-b9beb49da07947d8883b89d17e513bab
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115121B2

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