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 2279167노트

반응식

HRID 2279167 반응식
[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]

참가 물질

5

반응물 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

생성물 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-amide수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5189207cc3764aa9a5c248206ca0500b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133181B2

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