tert-butyl N-(5-amino-1H-pyrazol-3-yl)carbamate → methyl 3-(2-((tert-butoxycarbonyl)amino)-5,6-dihydropyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-7(8H)-yl)benzoate

HRID 1051548ノート

反応式

HRID 1051548 の反応式
CN([CH:4]=[C:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])[CH2:6]1)C.[NH2:22][C:23]1[NH:27][N:26]=[C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:24]=1>CCO>[C:31]([O:30][C:29]([NH:28][C:25]1[CH:24]=[C:23]2[N:22]=[C:10]3[CH2:9][CH2:8][N:7]([C:12]4[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=4)[C:15]([O:17][CH3:18])=[O:16])[CH2:6][C:5]3=[CH:4][N:27]2[N:26]=1)=[O:35])([CH3:32])([CH3:34])[CH3:33]

参加物

4

反応物 2

HCID 45091900tert-butyl N-(5-amino-1H-pyrazol-3-yl)carbamateHCID 86695813Methyl-3-(3-dimethylaminomethylene-4-oxopiperidin-1-yl)benzoate

生成物 1

HCID 121249644methyl 3-(2-((tert-butoxycarbonyl)amino)-5,6-dihydropyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-7(8H)-yl)benzoate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl 3-(3-((dimethylamino)methylene)-4-oxopiperidin-1-yl)benzoate (0.145 g, 0.503 mmol) and tert-Butyl (5-amino-1H-pyrazol-3-yl)carbamate (0.150 g, 0.756 mmol) in EtOH (4.0 mL) was stirred at 80° C. for 20 h. The mixture was cooled and concentrated. The residue was washed with MTBE and hexanes. Dried under high vacuum. A mixture of the title compound and methyl 3-(2-((tert-butoxycarbonyl)amino)-5,6-dihydropyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-7(8H)-yl)benzoate was afforded, which was separated by prep HPLC to afford the title compound (0.011 g) and methyl 3-(2-((tert-butoxycarbonyl)amino)-5,6-dihydropyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-7(8H)-yl)benzoate (0.050 g). Prep HPLC Method: Phenomex Luna 100×21.2 mm, 10 μM, C(18) column; Gradient of 55% H2O and 45% CH3CN; Flow Rate 1 mL/min.; uv @215 nm.

後処理

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. washThe residue was washed with MTBE and hexanes
  4. customDried under high vacuum
  5. additionA mixture of the title compound

出典と根拠

ORDレコード
ord-bee8a1a7f230403e83784477b5411815
出典データセット
uspto-grants-2016_07
特許番号
US09388181B2

反応ノート

読み込み中…