1,1'-Carbonyldiimidazole → HCID 53630190, compound

HRID 221883Notes

Reaction equation

HRID 221883 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:25]([N:27]2C=N[CH:29]=[CH:28]2)=[O:26])C=1.[N:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]2[CH:44]=CC(N)=[CH:41][CH:40]=2)=[CH:34][CH:33]=1>ClCCCl>[C:1]([C:5]1[CH:6]=[C:7]([NH:19][C:25]([NH:27][C:28]2[CH:29]=[CH:44][C:39]([O:38][C:35]3[CH:36]=[CH:37][N:32]=[CH:33][CH:34]=3)=[CH:40][CH:41]=2)=[O:26])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 13023603-tert-butyl-1-(4-nitrophenyl)-1H-pyrazol-5-amineHCID 115645894-(Pyridin-4-yloxy)aniline

Product 1

HCID 53630190HCID 53630190, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 5-tert-butyl-2-(4-nitrophenyl)-2H-pyrazol-3-ylamine (5.0 g, 19.2 mmol) in anhydrous DCE (2 mL) was added CDI (3.5 g, 21.1 mmol), and the reaction was stirred under N2 at room temperature for 18 h. 4-(Pyridin-4-yloxy)phenylamine (3.3 g, 17.7 mmol, Dumas et al., U.S. pat. appl. US2002065296 (2002)) in DCE (12 mL) was added to the reaction, and the solution was stirred under N2 at room temperature for 7 h. The reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The crude residue was purified by MPLC (1:1 hexanes/EtOAc) to give 5.6 g (68%) of the desired product. 1H-NMR (DMSO-d6) δ 9.21 (s, 1H), 8.68 (s, 1H), 8.43 (d, J=6.3 Hz, 2H), 8.36 (d, J=7.2 Hz, 2H), 7.90 (d, J=6.9 Hz, 2H), 7.50 (d, J=6.9 Hz, 2H), 7.09 (d, J=6.6 Hz, 2H), 6.86 (d, J=5.7 Hz, 2H), 6.44 (s, 1H), 1.29 (s, 9H); MS LC-MS [M+H]+=473, RT=2.60 min.

Workup

  1. stirringthe solution was stirred under N2 at room temperature for 7 h
  2. customThe reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated at reduced pressure
  6. customThe crude residue was purified by MPLC (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-393465ebc2b14ab0bd77b3d95829f2f9
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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