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

반응식

HRID 246137 반응식
[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]

참가 물질

7

반응물 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

생성물 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)-amide수율 75.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2a53dce436c84b478158f6d203aa44e1
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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