Diisopropylethylamine → 3-Chloro-N2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-pyrrole-2,5-dicarboxamide

HRID 1874969노트

반응식

HRID 1874969 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]([C:28]1[NH:32][C:31]([C:33]([OH:35])=O)=[C:30]([Cl:36])[CH:29]=1)=[O:27].[NH2:37][CH2:38][C:39]1[C:40]([F:56])=[C:41]([O:46][C:47]2[CH:48]=[C:49]([CH:52]=[C:53]([Cl:55])[CH:54]=2)[C:50]#[N:51])[C:42]([Cl:45])=[CH:43][CH:44]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:36][C:30]1[CH:29]=[C:28]([C:26]([NH2:25])=[O:27])[NH:32][C:31]=1[C:33]([NH:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([O:46][C:47]2[CH:48]=[C:49]([C:50]#[N:51])[CH:52]=[C:53]([Cl:55])[CH:54]=2)[C:40]=1[F:56])=[O:35]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 684804915-(Aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylic acid

생성물 1

HCID 594513903-Chloro-N2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-pyrrole-2,5-dicarboxamide수율 29.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

HATU (0.061 g, 0.161 mmol) was added to a solution of 5-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylic acid (0.030 g, 0.161 mmol), 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.050 g, 0.161 mmol), and DIPEA (0.028 mL, 0.161 mmol) in DMF (2 mL). This solution was stirred overnight at RT. The reaction mixture was partitioned between water and EtOAc. The organic layer was washed with a 15% solution of Na2CO3, dried over MgSO4, filtered and evaporated. Purification was accomplished by silica gel column chromatography (EtOAc/hexanes) to afford the title compound (0.023 g, 28%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.08 (br. s., 1H), 8.48-8.74 (m, 1H), 7.72-7.98 (m, 2H), 7.27-7.62 (m, 5H), 6.83 (d, 1H), 4.48 (d, 2H). LCMS: m/z 481.0 (M+1).

후처리

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe organic layer was washed with a 15% solution of Na2CO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification

출처 및 근거

ORD 기록
ord-f07daf14a82840e78108f34000ba7c72
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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