Methanamine, N-methoxy-, hydrochloride (1:1) → 6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide

HRID 2279167ノート

反応式

HRID 2279167 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:31](O)=[O:32])[C:18]3[C:23]([CH3:24])=[N:22][N:21]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[C:19]=3[N:20]=2)=[C:11]([F:34])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl.[CH3:45][NH:46][O:47][CH3:48]>ClCCl>[CH3:48][O:47][N:46]([CH3:45])[C:31]([C:17]1[C:18]2[C:23]([CH3:24])=[N:22][N:21]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)[C:19]=2[N:20]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[F:34])[CH:16]=1)=[O:32]

参加物

5

反応物 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 866803216-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

生成物 1

HCID 900139076-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (3.00 g) was dissolved in dichloromethane (50 mL), DIPEA (3.34 mL), N,O-dimethylhydroxylamine hydrochloride (0.63 g) and finally BEP (3.92 g) were added. The mixture was stirred at r.t. overnight, then extracted with sat. sodium carbonate solution, washed with 1N HCl and finally again with sodium carbonate solution. The solvent was evaporated and the residue was crystallized from methanol and filtered off giving 6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide (2.28 g, 70%) as a solid.

後処理

  1. additionwere added
  2. extractionextracted with sat. sodium carbonate solution
  3. washwashed with 1N HCl and finally again with sodium carbonate solution
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from methanol
  6. filtrationfiltered off

出典と根拠

ORDレコード
ord-5189207cc3764aa9a5c248206ca0500b
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

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