Diisopropylethylamine → [4-(4-Bromo-2,5-dichloro-phenoxy)-pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone

HRID 1025851

반응식

HRID 1025851 반응식
[Br:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([O:6][C:7]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:4]([Cl:19])[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH:53]1([N:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[NH:59][CH2:58][CH2:57]2)[CH2:55][CH2:54]1>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([O:6][C:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:12]=2[C:13]([N:59]2[C:60]3[C:65](=[CH:64][CH:63]=[CH:62][CH:61]=3)[N:56]([CH:53]3[CH2:55][CH2:54]3)[CH2:57][CH2:58]2)=[O:15])=[C:4]([Cl:19])[CH:3]=1

참가 물질

8

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)2회HCID 673204804-(4-Bromo-2,5-dichlorophenoxy)nicotinic acidHCID 673207551-Cyclopropyl-1,2,3,4-tetrahydroquinoxaline

생성물 1

HCID 53312111[4-(4-Bromo-2,5-dichloro-phenoxy)-pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 5.0 g (13.77 mmol) 4-(4-bromo-2,5-dichloro-phenoxy)-nicotinic acid in 30 mL N,N-dimethylformamide were added 5.50 g (14.46 mmol) O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, commercially available, CAS RN 148893-10-1) and 7.03 mL (41.32 mmol) N,N-diisopropylethylamine. To this brown solution was added 2.52 g (14.46 mmol) 1-cyclopropyl-1,2,3,4-tetrahydro-quinoxaline (Example 8, intermediate a), the resulting clear brown solution was stirred at room temperature for 17 hours and then poured on 120 mL water and 120 mL ethyl acetate. The resulting mixture was filtered, the filter cake was thoroughly washed with water and a very small amount of ethyl acetate to give after drying 6.55 g (92%) of the title compound as a brown solid. MS (ESI): m/z=520.1 [M+H]+.

후처리

  1. filtrationThe resulting mixture was filtered
  2. washthe filter cake was thoroughly washed with water
  3. customa very small amount of ethyl acetate to give
  4. dry with materialafter drying 6.55 g (92%) of the title compound as a brown solid

출처 및 근거

ORD 기록
ord-c43b11f54e784e8395a0e891346b74be
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729091B2

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