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 17108노트

반응식

HRID 17108 반응식
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

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 131728184HCID 131728184, 화합물

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c27a4768e6e9450ab1ff655919e0b491
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737279B2

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