Pyridine → HCID 86613805, compound

HRID 2378127Notes

Reaction equation

HRID 2378127 reaction equation
[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]([CH3:10])=[N:3]1.[CH:11]([O:14][C:15]([N:17]1[C:26]2[C:21](=N[C:23]([C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=2)[CH:20]([NH:31][CH2:32][C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=2)[CH2:19][CH:18]1[CH2:47][CH3:48])=[O:16])([CH3:13])[CH3:12].N1C=CC=C[CH:50]=1>ClCCl>[CH:11]([O:14][C:15]([N:17]1[C:26]2[C:21](=[CH:50][C:23]([C:27]([F:29])([F:30])[F:28])=[CH:24][CH:25]=2)[C@H:20]([N:31]([CH2:32][C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:40])[F:41])[CH:36]=[C:35]([C:43]([F:44])([F:46])[F:45])[CH:34]=2)[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH:5]=2)=[O:8])[CH2:19][C@@H:18]1[CH2:47][CH3:48])=[O:16])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chloride2×HCID 86613806HCID 86613806, compound

Product 1

HCID 86613805HCID 86613805, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Add a solution of 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (50 mg, 0.31 mmol) in dry dichloromethane (0.5 mL) to a solution of 4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (159 mg, 0.28 mmol) in dry dichloromethane (2 mL) and pyridine (0.045 mL, 0.56 mmol) at 0° C. Stir the mixture at room temperature for 3 h. Add a solution of 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (57 mg, 0.36 mmol) in dry dichloromethane (0.5 mL) and stir the mixture overnight. Remove the solvents under reduced pressure and purify the residue by silica gel flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (106 mg, 56%). MS (ES+): 680 (M+H).

Workup

  1. stirringstir the mixture overnight
  2. customRemove the solvents under reduced pressure
  3. custompurify the residue by silica gel flash chromatography
  4. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b3e7d685348e4aee9ebd726635e0db62
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

Loading…