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 56512

反応式

HRID 56512 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8f416dc8b4d6400f92d6519f712cb4e7
出典データセット
uspto-grants-2016_09
特許番号
US09434707B2

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