Diisopropylethylamine → 1-(4-(4-(2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl)piperazin-1-yl)butyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

HRID 2386171ノート

反応式

HRID 2386171 の反応式
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][CH2:8][C:7]1=[O:17].BrCCCCN1C2C=CC=CC=2CCCC1=O.[C:35]([C:39]1[N:44]=[C:43]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH:42]=[C:41]([C:51]([F:54])([F:53])[F:52])[N:40]=1)([CH3:38])([CH3:37])[CH3:36].[Na+].[Br-].C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[C:35]([C:39]1[N:44]=[C:43]([N:45]2[CH2:46][CH2:47][N:48]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[CH2:10][CH2:9][CH2:8][C:7]3=[O:17])[CH2:49][CH2:50]2)[CH:42]=[C:41]([C:51]([F:52])([F:53])[F:54])[N:40]=1)([CH3:38])([CH3:36])[CH3:37]

参加物

7

反応物 5

HCID 81531DiisopropylethylamineHCID 253881Sodium BromideHCID 183996102-(tert-Butyl)-4-(piperazin-1-yl)-6-(trifluoromethyl)pyrimidineHCID 431652441-(4-bromobutyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 617222001-(4-chlorobutyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

生成物 1

HCID 444074361-(4-(4-(2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl)piperazin-1-yl)butyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 1-(4-chlorobutyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one and 1-(4-bromobutyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (0.40 g), 2-tert-butyl-4-piperazin-1-yl-6-(trifluoromethyl)pyrimidine (1.59 mmol, 0.46 g, prepared as in DE 19735410), NaBr (7.94 mmol, 0.82 g), diisopropylethylamine (15.57 mmol, 2.01 g) and N-methylpyrrolidinone (0.6 ml) was heated at 120° C. for 5 hours. The suspension was then filtered, and the filtrate was evaporated to dryness. The residue was taken up in ethyl acetate and extracted with saturated brine. The organic phase was dried, the desiccant was filtered off, and the solution was evaporated to dryness. The residue was purified by chromatography on silica gel (eluent: dichloromethane/MeOH (0-100%), resulting in 0.58 g of the title compound.

後処理

  1. filtrationThe suspension was then filtered
  2. customthe filtrate was evaporated to dryness
  3. extractionextracted with saturated brine
  4. customThe organic phase was dried
  5. filtrationthe desiccant was filtered off
  6. customthe solution was evaporated to dryness
  7. customThe residue was purified by chromatography on silica gel (eluent

出典と根拠

ORDレコード
ord-9de8c70aecab49148f8da99249fa5d0a
出典データセット
uspto-grants-2012_09
特許番号
US08268815B2

反応ノート

読み込み中…