Water → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (cis-3-cyanomethyl-cyclopentyl)-amide

HRID 245918

反応式

HRID 245918 の反応式
C([N:4](CC)[CH:5]([CH3:7])[CH3:6])(C)C.[F:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([C:21]3[N:22]=[C:23]4[C:29]([C:30]([OH:32])=O)=[CH:28][N:27]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:24]4=[N:25][CH:26]=3)=[N:16][N:17]2[CH3:20])=[CH:13][CH:12]=1.CN(C(O[N:49]1N=N[C:51]2[CH:52]=[CH:53]C=N[C:50]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>FC(F)(F)C(O)=O.N[C@@H]1CC[C@H](CC#N)C1.CN(C=O)C>[C:50]([CH2:51][C@@H:52]1[CH2:53][CH2:6][C@H:5]([NH:4][C:30]([C:29]2[C:23]3[C:24](=[N:25][CH:26]=[C:21]([C:15]4[C:14]5[C:18](=[CH:19][C:11]([F:10])=[CH:12][CH:13]=5)[N:17]([CH3:20])[N:16]=4)[N:22]=3)[N:27]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:38])([CH3:39])[CH3:40])[CH:28]=2)=[O:32])[CH2:7]1)#[N:49]

参加物

7

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712796202-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

生成物 1

HCID 712855892-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (cis-3-cyanomethyl-cyclopentyl)-amide収率 94%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 18453414(cis-3-Amino-cyclopentyl)-acetonitrile trifluoroacetate溶媒

実験手順

In a round-bottomed flask, (cis-3-amino-cyclopentyl)-acetonitrile trifluoroacetate (crude from Step 6) was dissolved in DMF (1.3 ml) and N,N-diisopropylethylamine (0.65 ml, 3.72 mmol) was added. Then, 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (110 mg, 0.25 mmol) and HATU (104 mg, 0.27 mmol) were added. The yellow solution was stirred at room temperature for 48 h. Water and petroleum ether were added and the resulting suspension was filtered. The filter cake was washed with water and petroleum ether then dried under high vacuum to afford 128 mg (94%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (cis-3-cyanomethyl-cyclopentyl)-amide as an off-white powder.

後処理

  1. filtrationthe resulting suspension was filtered
  2. washThe filter cake was washed with water and petroleum ether
  3. customthen dried under high vacuum

出典と根拠

ORDレコード
ord-aca3186f0b79431b8442c235b246e711
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…