Diisopropylethylamine → 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1H-imidazol-2-yl)-amide

HRID 246137

反応式

HRID 246137 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21](O)=[O:22])=[CH:19][N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.S(O)(O)(=O)=O.[NH2:61][C:62]1[NH:63][CH:64]=[CH:65][N:66]=1.C(N(C(C)C)CC)(C)C>O.CN(C)C=O>[NH:63]1[CH:64]=[CH:65][N:66]=[C:62]1[NH:61][C:21]([C:20]1[C:14]2[C:15](=[N:16][CH:17]=[C:12]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:8]([CH3:11])[N:7]=3)[N:13]=2)[N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:19]=1)=[O:22]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712796712-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

生成物 1

HCID 712861702-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1H-imidazol-2-yl)-amide収率 75.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A solution of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (205 mg, 0.447 mmol), 1 mL of N,N-dimethylformamide and O-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (208 mg, 0.548 mmol) was stirred 10 min. To the solution was added freshly ground 2-aminoimidazole sulfate (62 mg, 0.468 mmol) and diisopropylethylamine (0.39 mL, 2.2 mmol). The flask was heated to 70° C. and the cloudy yellow solution was stirred 18.5 h, during which time a white precipitate formed. The mixture was allowed to cool, then treated with 20 mL of water. The precipitate was isolated by Buchner filtration, rinsing well with water and dried by air then in vacuo to afford 177 mg of impure 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1H-imidazol-2-yl)-amide as a pale yellow solid. MS: (M+H)+=523.

後処理

  1. customformed
  2. temperatureto cool
  3. customThe precipitate was isolated by Buchner filtration
  4. washrinsing well with water
  5. customdried by air

出典と根拠

ORDレコード
ord-2a53dce436c84b478158f6d203aa44e1
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

関連ノート

読み込み中…