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 1051548노트

반응식

HRID 1051548 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bee8a1a7f230403e83784477b5411815
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388181B2

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