Triethylamine → HCID 178473664, compound

HRID 1947445Notes

Reaction equation

HRID 1947445 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]([NH:18][OH:19])=[NH:17])=[CH:12][N:11]3[CH:20]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]([NH:18][O:19][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[NH:17])=[CH:12][N:11]3[CH:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178513230HCID 178513230, compound

Product 1

HCID 178473664HCID 178473664, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Fluoro-phenyl)-N-hydroxy-imidazo[1,2-a]pyridine-6-carboxamidine (example 56; 85.1 mg, 0.315 mmol) was dissolved in 5 ml DMF. The mixture was heated to 80° C. after addition of triethylamine (87.8 μl, 0.63 mmol) and ethyl chloroformate (33 μl, 0.34 mmol) for 2.5 hours. The mixture was evaporated. Ethyl acetate and water were added, the organic layer was separated, washed with water, dried and evaporated. The crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) to yield 48 mg (45%) of the desired product. MS: M+H+=343.05.

Workup

  1. customThe mixture was evaporated
  2. additionEthyl acetate and water were added
  3. customthe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-d972b9a90f0849a8adc9f7364a96ceaf
Source dataset
uspto-grants-2013_03
Patent number
US08399476B2

Reaction notes

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