di-tert-butyl 5-amino-3-oxo-1H-indazole-1,2(3H)-dicarboxylate → HCID 178440357, compound

HRID 1987637Notes

Reaction equation

HRID 1987637 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]/[C:4](=[C:12]2/[C:13]([CH2:18][CH2:19][CH3:20])=[N:14][NH:15][C:16]/2=[O:17])/[CH:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27](C(OC(C)(C)C)=O)[N:26](C(OC(C)(C)C)=O)[C:25]2=[O:45]>C(O)C>[O:17]=[C:16]1[NH:15][N:14]=[C:13]([CH2:18][CH2:19][CH3:20])/[C:12]/1=[C:4]1/[NH:5][C:6]2[C:11]([C:2]([NH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[NH:27][NH:26][C:25]4=[O:45])=[CH:3]/1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 69055338di-tert-butyl 5-amino-3-oxo-1H-indazole-1,2(3H)-dicarboxylateHCID 178440352HCID 178440352, compound

Product 1

HCID 178440357HCID 178440357, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

(Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-propyl-1H-pyrazol-5(4H)-one (0.03 g, 0.1 mmol) was dissolved in ethanol (1.5 mL) and di-tert-butyl 5-amino-3-oxo-1H-indazole-1,2(3H)-dicarboxylate (0.044 g, 0.12 mmol) was added. The reaction mixture was heated to 170° C. using a microwave reactor for 30 minutes. The mixture was concentrated and purified by LC-MS to give the title compound of Example 51. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.51 (t, J=6.95 Hz, 3H) 1.26-1.33 (m, 2H) 2.39 (dd, J=9.09, 3.28 Hz, 2H) 6.41 (s, 1H) 7.38 (dd, J=8.72, 1.64 Hz, 1H) 7.45-7.51 (m, 1H) 7.67-7.73 (m, 2H) 7.90-7.98 (m, 2H) 8.59 (d, J=7.58 Hz, 1H) 10.49 (s, 1H) 11.79 (s, 1H); ESI-MS: m/z calc'd for C22H20N6O2 400.43. found 401.3 (M+H)+.

Workup

  1. customfor 30 minutes
  2. concentrationThe mixture was concentrated
  3. custompurified by LC-MS

Sources & evidence

ORD record
ord-f817e9b2a4694744b9938ff6ecada8e0
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

Loading…