1,10-Phenanthroline → HCID 86759850, compound

HRID 497429Notes

Reaction equation

HRID 497429 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH3:18])[C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.FC(F)(F)C(NC[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[C:35]2[C:36](=O)[N:37]([C:40]3[CH:45]=[CH:44][C:43](I)=[CH:42][C:41]=3F)[CH2:38][CH2:39][C:34]=2[C:33]([C:49]([F:52])([F:51])[F:50])=[N:32]1)=O.[C:55]([O-:58])([O-])=O.[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=C[CH:62]=1>[Cu]I.CS(C)=O>[CH3:55][O:58][C:29]1[CH:30]=[CH:25][C:26]([N:31]2[C:35]3[C:36](=[CH2:62])[N:37]([C:40]4[CH:41]=[CH:42][C:43]([N:1]5[CH:5]=[CH:4][N:3]=[C:2]5[CH2:6][N:7]([CH3:18])[C:8](=[O:17])[O:9][CH2:10][C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)=[CH:44][CH:45]=4)[CH2:38][CH2:39][C:34]=3[C:33]([C:49]([F:52])([F:50])[F:51])=[N:32]2)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 12125407Benzyl [(1H-imidazol-2-yl)methyl]methylcarbamateHCID 86759851HCID 86759851, compound

Product 1

HCID 86759850HCID 86759850, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

Benzyl 1H-imidazol-2-ylmethyl(methyl)carbamat (1.17 g, 4.76 mmol) from Part E, 1-[2-trifluoroacetamidomethyl-phenyl]-3-trifluoromethyl-6-[4-Iodo-2-fluorophenyl]-1,4,5,6-tetrahydropyrazolo-[3,4-c]-pyridin-7-one from Part D (1.63 g, 3.18 mmol), CuI (0.12 9, 20%), K2CO3 (0.66 g, 4.76 mmol), 1,10-phenanthroline (56 mg, 20%) were added together with 100 mL of DMSO. The mixture was degassed and then heated at 130° C. under N2 for 12 h. The mixture was cooled and aqueous NH4OH (200 mL of of 10% NH4OH) was added. The mixture was filtered through Celite® and washed with EtOAc. The two layers were separated and the aqueous layer was extracted with EtOAc. The combined EtOAc mixture was washed with brine, dried over MgSO4, concentrated, and chromatographed with EtOAc to give 1.34 g of the desired product (66.9%). MS (ES+): 631.3, (M+H)+.

Workup

  1. customThe mixture was degassed
  2. temperatureThe mixture was cooled
  3. additionaqueous NH4OH (200 mL of of 10% NH4OH) was added
  4. filtrationThe mixture was filtered through Celite®
  5. washwashed with EtOAc
  6. customThe two layers were separated
  7. extractionthe aqueous layer was extracted with EtOAc
  8. washThe combined EtOAc mixture was washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customchromatographed with EtOAc

Sources & evidence

ORD record
ord-8373de6249c24b8faf730d386b505b64
Source dataset
uspto-grants-2005_09
Patent number
US06949550B2

Reaction notes

Loading…