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Ethylenediamine → 2-[6-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide

HRID 246258
ノート
印刷プレビュー

反応式

HRID 246258 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[C:29]5[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=5)[N:23]([CH2:31][CH2:32][N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)[N:22]=4)[N:19]=3)[N:14](COCC[Si](C)(C)C)[CH:13]=2)=[O:11])[CH3:8])[CH:2]=1.FC(F)(F)C(O)=O.C(N)CN>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[C:29]5[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=5)[N:23]([CH2:31][CH2:32][N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)[N:22]=4)[N:19]=3)[NH:14][CH:13]=2)=[O:11])[CH3:8])[CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712884332-[6-Chloro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide

生成物 1

HCID 712884282-[6-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide収率 71.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-[6-Chloro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide (50 mg, 0.076 mmol) was combined with dichloromethane (1 mL) and trifluoroacetic acid (0.17 ml, 2.27 mmol) was added. After stirring for 2 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane (1 mL) and ethylenediamine (0.15 ml, 2.27 mmol) was added. The reaction mixture was stirred for 20 min then concentrated in vacuo and the residue was triturated with water (2 mL). The precipitate was filtered, washed with water and dried to afford 29 mg (68%) of 2-[6-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide as a yellow solid. MS: (M+H)+=531; 1H NMR (DMSO-d6) δ: 9.11 (s, 1H), 8.71 (br. s., 1H), 8.43-8.58 (m, 3H), 8.29-8.38 (m, 1H), 8.05 (s, 1H), 7.86 (d, J=7.3 Hz, 1H), 7.36 (br. s., 1H), 7.15 (d, J=8.3 Hz, 1H), 5.35 (t, J=6.9 Hz, 1H), 4.65 (br. s., 2H), 3.50 (br. s., 4H), 3.33 (br. s., 4H), 2.84 (br. s., 2H), 1.68 (d, J=6.3 Hz, 3H).

後処理

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (1 mL)
  4. stirringThe reaction mixture was stirred for 20 min
  5. concentrationthen concentrated in vacuo
  6. customthe residue was triturated with water (2 mL)
  7. filtrationThe precipitate was filtered
  8. washwashed with water
  9. customdried

出典と根拠

ORDレコード
ord-e3b74535b5e94ac3ba6c4797019f6ea2
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658646B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート