tert-butyl 4-amino-1H-pyrazole-1-carboxylate → 1-(2-(2-(2-(1H-Pyrazol-4-ylamino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592394Notes

Reaction equation

HRID 592394 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17]2)[C:5]([Cl:22])=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:25]=[N:26][N:27](C(OC(C)(C)C)=O)[CH:28]=1>CO.O>[NH:26]1[CH:25]=[C:24]([NH:23][C:2]2[N:7]=[C:6]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:16]3([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17]3)[C:5]([Cl:22])=[CH:4][N:3]=2)[CH:28]=[N:27]1

Participants

4

Reactant 2

HCID 59587648tert-butyl 4-amino-1H-pyrazole-1-carboxylateHCID 867122951-(2-(2-(2,5-Dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

Product 1

HCID 732967141-(2-(2-(2-(1H-Pyrazol-4-ylamino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.070 g, 0.21 mmol) and tert-butyl 4-amino-1H-pyrazole-1-carboxylate (0.11 g, 0.63 mmol) was stirred in MeOH:water (10:1 ratio, 4 mL) at 70° C. for 2 hours and then at 90° C. for 16 hours. The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Combiflash Rf, 0-15% MeOH in DCM) to give the title compound 19 as a light yellow solid (0.015 g, 19%). 1H NMR (300 MHz, d6-DMSO) δ 0.93-1.02 (m, 2H), 1.38-1.49 (m, 2H), 3.04-3.16 (m, 4H), 6.03 (brs, 1H), 6.98 (brs, 1H), 7.18-7.39 (m, 4H), 7.48-7.72 (m, 1H), 7.79-8.00 (m, 1H), 8.37 (s, 1H), 9.62 (s, 1H). LCMS-C: rt 4.92 min; m/z 383 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by silica gel column chromatography (Combiflash Rf, 0-15% MeOH in DCM)

Sources & evidence

ORD record
ord-f84f43d6a87e40e78873217764b7df84
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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