Dimethylamine → HCID 67274220, compound

HRID 600627Notes

Reaction equation

HRID 600627 reaction equation
Br.[C:2]([C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=O)=[CH:14][N:13]2[CH:21]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[CH2:23][N:24]=[C:25]=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CNC>CN(C=O)C.C1COCC1>[C:2]([C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:24]([CH3:25])[CH3:23])=[O:20])=[CH:14][N:13]2[CH:21]=1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67273587HCID 67273587, compound

Product 1

HCID 67274220HCID 67274220, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 0.21 g of 2-benzoylimidazo[1,2-a]pyridine-6-carboxylic acid hydrobromide, 0.35 g of EDCI hydrochloride and 0.294 g of HOBT in 7 mL of DMF is stirred for 30 minutes at 20° C., followed by addition of 1 mL of a 1 M solution of dimethylamine in THF, and the mixture is stirred for 2 hours at 20° C. The reaction mixture is concentrated to dryness and then taken up in 100 mL of water and 200 mL of ethyl acetate. The organic phase is separated out, dried and evaporated. The residue is purified by flash chromatography on a column of 20 g of silica, eluting with a 99/1 mixture of dichloromethane and methanol. The fractions containing the expected product are combined and concentrated under vacuum to give 40 mg of 2-benzoyl-N,N-dimethylimidazo[1,2-a]pyridine-6-carboxamide in the form of a beige-colored solid.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customThe organic phase is separated out
  3. customdried
  4. customevaporated
  5. customThe residue is purified by flash chromatography on a column of 20 g of silica
  6. washeluting with a 99/1 mixture of dichloromethane and methanol
  7. additionThe fractions containing the expected product
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c73454471e2348efa10544107c922462
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

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