2,2-Difluoro-1,3-benzodioxole-4-carbonyl chloride → 5-[(2,2-Difluoro-1,3-benzodioxol-4-yl)carbonyl]-1-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

HRID 2177578Notes

Reaction equation

HRID 2177578 reaction equation
[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:16][C:17]1([F:29])[O:21][C:20]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26](Cl)=[O:27])[C:19]=2[O:18]1>C(Cl)(Cl)Cl>[F:29][C:17]1([F:16])[O:21][C:20]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([N:12]3[CH2:13][CH2:14][C:15]4[N:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH:8]=[N:9][C:10]=4[CH2:11]3)=[O:27])[C:19]=2[O:18]1

Participants

4

Reactant 2

HCID 27740622,2-Difluoro-1,3-benzodioxole-4-carbonyl chlorideHCID 1315025687673-89-0

Product 1

HCID 862707235-[(2,2-Difluoro-1,3-benzodioxol-4-yl)carbonyl]-1-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridineYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the product of Example 50, Step A (28 mg, 0.141 mmol) and TEA (23 μL, 0.169 mmol) in CHCl3 (1 mL) cooled to 0° C. was added 2,2-difluoro-1,3-benzodioxole-4-carbonyl chloride (34 mg, 0.155 mmol). The reaction was warmed to room temperature and stirred overnight. The crude reaction mixture purified on 12 g SiO2 column with 0-4% NH3/MeOH CH2Cl2 to give the desired compound (43 mg, 80%). MS (ESI): mass calcd. for C20H15F2N3O3, 383.1. m/z found, 384.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.71-7.39 (m, 4H), 7.36-7.09 (m, 5H), 4.88 (s, 1H), 4.58 (t, J=1.6 Hz, 2H), 4.08 (t, J=5.9 Hz, 2H), 3.66 (t, J=5.6 Hz, 1H), 2.86-2.74 (m, 3H).

Workup

  1. customThe crude reaction mixture
  2. custompurified on 12 g SiO2 column with 0-4% NH3/MeOH CH2Cl2

Sources & evidence

ORD record
ord-a8aa5e4893f9436096f9a5a2a84d68e1
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

Loading…