Ammonia → HCID 66882585, compound

HRID 505230Notes

Reaction equation

HRID 505230 reaction equation
[Cl:1][C:2]1[C:3]([CH2:16][C:17]([OH:19])=O)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][N:13]([CH3:15])[CH3:14])=[N:5]2.C(C1NC=CN=1)(C1[NH:23]C=CN=1)=O.N>Cl.CN(C)C=O>[Cl:1][C:2]1[C:3]([CH2:16][C:17]([NH2:23])=[O:19])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][N:13]([CH3:15])[CH3:14])=[N:5]2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 66883065HCID 66883065, compound

Product 1

HCID 66882585HCID 66882585, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Hydrochloric acid (4 M in dioxane, 8 drops) was added to a solution of the above (6-chloro-3-dimethylaminomethyl-quinoxalin-5-yl)-acetic acid in N,N-dimethylformamide (3 ml). A solution of carbonyl diimidazole (188 mg, 1.16 mmol, 1.2 equiv) in N,N-dimethylformamide (5 ml) was added, and the mixture was stirred at room temperature for 1 hour. Concentrated aqueous ammonia (25%, 10 ml) was added, and after 10 minutes at room temperature, volatiles were removed in vacuo. The residue was purified via flash chromatorgraphy (gradient of CH2Cl2/MeOH 95:5 to 70:30) to afford the title compound (180 mg, 67%) as a foam. 1H NMR (400 MHz, d6-DMSO): δ=9.02 (s, 1H), 8.06 (d, J=9.2 Hz, 1H), 7.94 (d, J=9.2 Hz, 1H), 7.54 (br s, 1H), 6.98 (br s, 1H), 4.7-4.5 (br, 2H), 4.32 (s, 2H), 2.78 (br s, 6H). MS (ES+): 279.2 (M+H)+.

Workup

  1. waitafter 10 minutes at room temperature
  2. customvolatiles were removed in vacuo
  3. customThe residue was purified via flash chromatorgraphy (gradient of CH2Cl2/MeOH 95:5 to 70:30)

Sources & evidence

ORD record
ord-23a5a1a8cac041b0b6508701ddfd6681
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

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