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Triethylamine → N-methoxy-N-methyl-5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxamide

HRID 869716
ノート
印刷プレビュー

反応式

HRID 869716 の反応式
[N:1]1([C:6]2[CH:11]=[C:10]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:9]3[N:19]=[C:20]([C:22]([OH:24])=O)[CH:21]=[C:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:38][NH:39][O:40][CH3:41].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:41][O:40][N:39]([CH3:38])[C:22]([C:20]1[CH:21]=[C:8]2[N:7]=[C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:11]=[C:10]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:9]2[N:19]=1)=[O:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 674075435-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

生成物 1

HCID 86674519
N-methoxy-N-methyl-5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (2.15 g, 5.26 mmol) in dichloromethane (60 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.27 g, 13.0 mmol), N,O-dimethylhydroxylamine hydrochloride (2.49 g, 13.0 mmol), and triethylamine (2.30 g, 22.7 mmol) at 0° C. After being stirred for 17 h at room temperature, the reaction mixture was poured into saturated sodium bicarbonate. The mixture was extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1) to give N-methoxy-N-methyl-5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxamide. MS (APCI): m/z 375 (M+H).

後処理

  1. extractionThe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1)

出典と根拠

ORDレコード
ord-f60e5036c27d4171abcb2bb1e82cb41c
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08969376B2

反応ノート

読み込み中…

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