Triethylamine → HCID 69521992, compound

HRID 968764Notes

Reaction equation

HRID 968764 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH:14][CH3:15])[CH2:8][CH2:7]1.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([Cl:34])=[O:33]>C1COCC1>[ClH:34].[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][N:14]([CH3:15])[C:32](=[O:33])[C:31]2[CH:35]=[CH:36][CH:37]=[C:29]([O:28][CH3:27])[CH:30]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 69311930HCID 69311930, compound

Product 1

HCID 69521992HCID 69521992, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product of Step c (0.145 g) and triethylamine (0.224 ml) in THF (3 ml) at 0° C. was added a solution 3-methoxybenzoyl chloride (0.083 ml) in THF (2 ml). The mixture was stirred for 1 hour then partitioned between ethyl acetate and water. The organic layer was separated and dried with MgSO4 and the solvent removed by evaporation. Purification by reverse phase HPLC (with a gradient eluent system 25% MeCN/NH4OAc(aq) (0.1%) to 95% MeCN//NH4OAc(aq) (0.1%)) evaporation of solvent and the residue was dissolved in diethyl ether and HCl (1 ml 1M solution in diethyl ether) added. Filtration gave the title compound (0.137 g).

Workup

  1. customthen partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. customthe solvent removed by evaporation
  5. customPurification by reverse phase HPLC (with a gradient eluent system 25% MeCN/NH4OAc(aq) (0.1%) to 95% MeCN//NH4OAc(aq) (0.1%))
  6. customevaporation of solvent
  7. dissolutionthe residue was dissolved in diethyl ether
  8. additionHCl (1 ml 1M solution in diethyl ether) added
  9. filtrationFiltration

Sources & evidence

ORD record
ord-be09dc49abcc471caa8fb028ac5cd617
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

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