1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 8-chloro-N-[(4-cyano-2,5-dimethylphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide

HRID 1028399Notes

Reaction equation

HRID 1028399 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:12]=[C:13]([C:15]([OH:17])=O)[N:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.CN(C)CCCN=C=NCC.[C:30]([C:32]1[C:37]([CH3:38])=[CH:36][C:35]([S:39]([NH2:42])(=[O:41])=[O:40])=[C:34]([CH3:43])[CH:33]=1)#[N:31]>C(O)(C)(C)C.ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:3]2[N:4]([CH:12]=[C:13]([C:15]([NH:42][S:39]([C:35]3[CH:36]=[C:37]([CH3:38])[C:32]([C:30]#[N:31])=[CH:33][C:34]=3[CH3:43])(=[O:40])=[O:41])=[O:17])[N:14]=2)[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 39288178-Chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acidHCID 666452604-Cyano-2,5-dimethylbenzenesulfonamide

Product 1

HCID 498188088-chloro-N-[(4-cyano-2,5-dimethylphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamideYield 37.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To a solution of 8-chloro-6-(trifluoromethyl)imidazo[1,2-c]pyridine-2-carboxylic acid (2.5 g, 9.5 mmol, prepared as described in Example 1 Step C) in t-butanol (70 mL) and dichloromethane (70 mL) was added 4-(dimethylamino)pyridine (3.47 g, 28.4 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.54 g, 23.7 mmol). The reaction mixture was stirred for 15 min after which time 4-cyano-2,5-dimethylbenzenesulfonamide (1.85 g, 8.85 mmol) was added, and stirring was continued at room temperature overnight. Dichloromethane (200 mL) was then added, the mixture was washed with 1 N hydrochloric acid (3×100 mL), the organic phase was collected and dried over magnesium sulfate and then concentrated under reduced pressure to afford a solid. The solid was isolated by filtration, rinsed with diethyl ether, and recrystallized from hexane/ethyl acetate to afford 1.5 g of the title compound, a compound of the present invention, as a solid, m.p. 228-229° C. 1H NMR (CDCl3) δ 9.97 (br s, 1H), 8.47 (s, 1H), 8.26 (s, 1H), 8.24 (s, 1H), 7.56 (s, 1H), 7.54 (s, 1H), 2.71 (s, 3H), 2.63 (s, 3H).

Workup

  1. additionwas added
  2. washthe mixture was washed with 1 N hydrochloric acid (3×100 mL)
  3. customthe organic phase was collected
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford a solid
  7. customThe solid was isolated by filtration
  8. washrinsed with diethyl ether
  9. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-129dbc3a16aa470084e3d9a41ad9eb34
Source dataset
uspto-grants-2014_05
Patent number
US08735588B2

Reaction notes

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