Dimethylformamide → [2-Amino-6-(1-methyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

HRID 30131ノート

反応式

HRID 30131 の反応式
F[C:2](F)(F)C(O)=O.[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:16])=[CH:13]N=[C:11]([NH:26][CH:27]2[CH2:32]CNC[CH2:28]2)[N:10]=1.C(=O)([O-])[O-].[K+].[K+].IC.[CH3:41][N:42]([CH3:45])[CH:43]=O>C(OCC)(=O)C>[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:16])=[CH:13][CH:2]=[C:11]([NH:26][CH:27]2[CH2:28][CH2:43][N:42]([CH3:45])[CH2:41][CH2:32]2)[N:10]=1

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21070627[4-Amino-2-(piperidin4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone trifluoroacetic acid salt

生成物 1

HCID 11501336[2-Amino-6-(1-methyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone収率 24%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone trifluoroacetic acid salt (0.0575 mmol, Example 22) in N,N-dimethylformamide (1.5 mL) were added potassium carbonate (55.6 mg, 0.4024 mmol, Aldrich) and iodomethane (14.8 mg, 0.104 mmol, Aldrich 99.5%) in N,N-dimethylformamide (0.35 mL). The reaction was stirred at 0° C. for 4 hrs. The resulting mixture was diluted with ethyl acetate (30 mL), washed with water, brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified on reversed phase HPLC to give [2-Amino-6-(1-methyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid (4.8 mg, 24% yield). HRMS, observed: 358.1810, Calcd for M+: 358.1805.

後処理

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified on reversed phase HPLC

出典と根拠

ORDレコード
ord-a5fd57a524414ea9b654591ec4def49b
出典データセット
uspto-grants-2008_09
特許番号
US07423051B2

反応ノート

読み込み中…