1-Hydroxybenzotriazole → HCID 44124031, compound

HRID 600634Notes

Reaction equation

HRID 600634 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[CH:7]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Cl.[CH3:37][NH:38][O:39][CH3:40]>ClCCl.O.C(N(CC)CC)C>[CH3:40][O:39][N:38]([CH3:37])[C:11]([C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]2[CH:8]=1)=[O:13]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27576146-chloroimidazo[1,2-a]pyridine-2-carboxylic acid

Product 1

HCID 44124031HCID 44124031, compoundYield 62.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 0.784 g of 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid in 12 mL of dichloromethane are added 1.67 mL of triethylamine, 1.53 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.08 g of 1-hydroxybenzotriazole. The reaction mixture is stirred for 20 minutes at room temperature. 0.39 g of N,O-dimethylhydroxylamine hydrochloride is added. The reaction mixture is stirred for 4 hours at room temperature. 60 mL of dichloromethane and 30 mL of water are added. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered, evaporated to dryness under reduced pressure, and then purified on a column of silica, eluting with a 95/5 mixture by volume of dichloromethane and methanol. The fractions containing the product are combined and concentrated to dryness under reduced pressure to give 0.6 g of N-methoxy-N-methyl-6-chloroimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. stirringThe reaction mixture is stirred for 4 hours at room temperature
  2. customAfter separation of the phases
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. custompurified on a column of silica
  7. washeluting with a 95/5 mixture by volume of dichloromethane and methanol
  8. additionThe fractions containing the product
  9. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b0b6798e70964e929fc875a3d4a92655
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

Loading…