Methanamine, N-methoxy-, hydrochloride (1:1) → N,2-dimethoxy-N-methyl-2-(4-(1-(tris(4-methoxyphenyl)methyl)-1H-pyrazol-4-yl)phenyl)acetamide

HRID 2359171

반응식

HRID 2359171 반응식
[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][N:16]([C:18]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)=[CH:9][CH:8]=1)[C:4]([O-])=[O:5].[K+].C(N(C(C)C)CC)(C)C.COCCN(S(F)(F)F)CCOC.Cl.[CH3:67][NH:68][O:69][CH3:70]>CN(C=O)C.O>[CH3:70][O:69][N:68]([CH3:67])[C:4](=[O:5])[CH:3]([O:2][CH3:1])[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[N:15][N:16]([C:18]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)([C:27]3[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)[CH:17]=2)=[CH:11][CH:12]=1

참가 물질

7

반응물 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 67388959potassium 2-methoxy-2-(4-(1-(tris(4-methoxyphenyl)methyl)-1H-pyrazol-4-yl)phenyl)acetate

생성물 1

HCID 58432018N,2-dimethoxy-N-methyl-2-(4-(1-(tris(4-methoxyphenyl)methyl)-1H-pyrazol-4-yl)phenyl)acetamide수율 37.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To an ice-cold solution of potassium 2-methoxy-2-(4-(1-(tris(4-methoxyphenyl)methyl)-1H-pyrazol-4-yl)phenyl)acetate (1.25 g, 2.1 mmol) in anhydrous DMF (10 mL) under argon was added diisopropylethylamine (0.54 mL, 3.1 mmol) and bis(2-methoxyethyl)aminosulfur trifluoride (0.46 mL, 2.5 mmol) dropwise. The reaction was stirred for 30 min then N,O-dimethylhydroxylamine hydrochloride (0.303 g, 3.1 mmol) was added. After stirring for a further 15 min over an ice bath, the mixture was allowed to warm to room temperature and stirred for 3.5 hrs. H2O was added and the mixture was extracted with EtOAc. The combined organics were washed with H2O, saturated aqueous NH4Cl, saturated aqueous NaHCO3, and brine then dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (45-90% EtOAc-hexanes; EtOAc containing 1% Et3N) to give N,2-dimethoxy-N-methyl-2-(4-(1-(tris(4-methoxyphenyl)methyl)-1H-pyrazol-4-yl)phenyl)acetamide (0.478 g from two reactions, 32% yield overall).

후처리

  1. stirringAfter stirring for a further 15 min over an ice bath
  2. stirringstirred for 3.5 hrs
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organics were washed with H2O, saturated aqueous NH4Cl, saturated aqueous NaHCO3, and brine
  5. dry with materialthen dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography (45-90% EtOAc-hexanes; EtOAc containing 1% Et3N)

출처 및 근거

ORD 기록
ord-f1f554ddd0de4d4abc6ba4fa35999162
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685975B2

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