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 506500노트

반응식

HRID 506500 반응식
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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-76efdb8490834b2b897dd9ba22b01bbe
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786105B2

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