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 1051548Notes

Reaction equation

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]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

temperatureThe mixture was cooled
concentrationconcentrated
washThe residue was washed with MTBE and hexanes
customDried under high vacuum
additionA mixture of the title compound

Sources & evidence

ORD record: ord-bee8a1a7f230403e83784477b5411815
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388181B2

Reaction notes

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