Diisopropylethylamine → HCID 58386374, compound

HRID 74648Notes

Reaction equation

HRID 74648 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.Cl[C:29]1[N:34]=[CH:33][N:32]=[C:31]([C:35]([N:37]2[C:45]3[C:40](=[CH:41][C:42]([F:46])=[CH:43][CH:44]=3)[CH:39]=[CH:38]2)=[O:36])[CH:30]=1>CN(C=O)C>[F:46][C:42]1[CH:41]=[C:40]2[C:45](=[CH:44][CH:43]=1)[N:37]([C:35]([C:31]1[N:32]=[CH:33][N:34]=[C:29]([N:3]3[CH2:4][CH2:5][CH:6]([N:9]4[C:17]5[C:12](=[N:13][CH:14]=[CH:15][CH:16]=5)[NH:11][C:10]4=[O:18])[CH2:7][CH2:8]3)[CH:30]=1)=[O:36])[CH:38]=[CH:39]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 58386546HCID 58386546, compound

Product 1

HCID 58386374HCID 58386374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

75.0 mg (0.26 mmol) 1-piperidin-4-yl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one dihydrochloride and 150 μL (0.87 mmol) DIPEA were added to 70 mg (0.25 mmol) (6-chloropyrimidin-4-yl)-(5-fluoroindol-1-yl)-methanone in 5 mL DMF. The reaction mixture was stirred overnight at RT and then evaporated down i. vac. The residue was taken up in 20 mL water and stirred for 10 min. The precipitate was suction filtered, dissolved in 2.5 mL DMF and purified by preparative HPLC. The product fractions were combined and concentrated by rotary evaporation using the rotary evaporator.

Workup

  1. customevaporated down i
  2. stirringstirred for 10 min
  3. filtrationfiltered
  4. dissolutiondissolved in 2.5 mL DMF
  5. custompurified by preparative HPLC
  6. concentrationconcentrated by rotary evaporation
  7. customthe rotary evaporator

Sources & evidence

ORD record
ord-bcbdd42cadc44401990c86a22a098426
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

Loading…