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

HRID 1025851

反応式

HRID 1025851 の反応式
[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

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2 回HCID 673204804-(4-Bromo-2,5-dichlorophenoxy)nicotinic acidHCID 673207551-Cyclopropyl-1,2,3,4-tetrahydroquinoxaline

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-c43b11f54e784e8395a0e891346b74be
出典データセット
uspto-grants-2014_05
特許番号
US08729091B2

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