Trifluoroacetic acid → n-[6-[1,6-Dihydro-1-methyl-4-(methylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-2-pyridinyl]-acetamide

HRID 17108ノート

反応式

HRID 17108 の反応式
C(O[C:6](=O)[N:7]([C:9]1[N:14]=[C:13]2[NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:27])[CH3:26])[N:19]=3)=[CH:17][C:12]2=[C:11]2[N:28]([CH3:31])[CH:29]=[N:30][C:10]=12)C)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:31][N:28]1[C:11]2=[C:12]3[CH:17]=[C:16]([C:18]4[N:19]=[C:20]([NH:24][C:25](=[O:27])[CH3:26])[CH:21]=[CH:22][CH:23]=4)[NH:15][C:13]3=[N:14][C:9]([NH:7][CH3:6])=[C:10]2[N:30]=[CH:29]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 131728184HCID 131728184、化合物

生成物 1

HCID 57394935n-[6-[1,6-Dihydro-1-methyl-4-(methylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-2-pyridinyl]-acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A436.2 (55 mg, 0.13 mmol), was dissolved in DMA (5 mL) and the solution heated to 70° C. One equivalent of 1.0M potassium t-butoxide in THF (0.14 ml, 0.14 mmol) was quickly added and the reaction heated at 70° C. for thirty minutes. A second equivalent of 1.0M potassium t-butoxide in THF (0.14 ml, 0.14 mmol) was quickly added and the reaction mixture stirred an additional thirty minutes. The reaction mixture was concentrated in vacuo. The crude product residue was chromatographed on Silica Gel (230-400 Mesh) eluting with 2-5% MeOH/CH2Cl2 to give the Boc-protected intermediate, tert-butyl-7-(6-acetamidopyridin-2-yl)-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-4-yl(methyl)carbamate as an off-white solid. (26 mg, 60% yield). The solid was dissolved in methylene chloride (0.5 mL) and trifluoroacetic acid (0.5 mL) was added and the reaction mixture stirred for 0.25 h. The solvent was evaporated under reduced pressure to provide A436 (20 mg, 60%). M+H+=336.34 1H NMR (400 MHz) MEOD δ 9.20 (s, 1H), 8.02 (m, 1H), 7.78 (m, 1H), 7.71 (d, 1H), 7.56 (s, 1H), 4.33 (s, 3H), 3.45 (s, 3H), 2.19 (s, 3H).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customto provide A436 (20 mg, 60%)

出典と根拠

ORDレコード
ord-c27a4768e6e9450ab1ff655919e0b491
出典データセット
uspto-grants-2010_06
特許番号
US07737279B2

反応ノート

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