Dichloromethane → HCID 24983902, compound

HRID 1014704Notes

Reaction equation

HRID 1014704 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1.B(O)(O)[C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH2:29])=[O:28])=[CH:23][CH:22]=1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O>[O:11]=[C:9]1[NH:10][C:5]2=[N:4][CH:3]=[C:2]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH2:29])=[O:28])=[CH:23][CH:22]=3)[N:7]=[C:6]2[N:8]1[CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27378114-Aminocarbonylphenylboronic acidHCID 86626416HCID 86626416, compound

Product 1

HCID 24983902HCID 24983902, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(2-oxo-3-(2-(Tetrahydro-2H-pyran-4-yl)ethyl)-2,3-dihydro-1H-imidazol-[4,5-b]pyrazin-5-yl)benzamide. 6-Bromo-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.400 g, 1.22 mmol), 4-carboxamide-phenylboronic acid (0.241 g, 1.46 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.098 g, 0.12 mmol), potassium phosphate (1.03 g, 4.88 mmol), water (2 ml) and dimethylformamide (7 mL) were reacted according to General Procedure B. The solution was condensed under reduced pressure and the product was crystallized from dichloromethane to give (0.400 g, 89% yield). 1H NMR (400 MHz, CD3OD) δ 8.54 (s, 1H) 8.40 (s, 1H), 8.09 (d, J=8.4, 2H), 7.94 (d, J=8.4, 1H), 4.08 (t, J=6.8, 2H), 3.92 (dd, J=11.2, 3.2, 2H), 3.64 (m, 2H), 1.83 (m, 4H), 1.59 (m, 1H), 1.38 (qd, J=12.8, 4.4, 2H); MS (ESI) m/z 368.4 [M+1]+; mp 233-236° C.

Workup

  1. customcondensed under reduced pressure
  2. customthe product was crystallized from dichloromethane
  3. customto give (0.400 g, 89% yield)

Sources & evidence

ORD record
ord-6af5f8c6f5a94a26a8cfd58ee63fdc35
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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