Water → HCID 22479271, compound

HRID 2182619Notes

Reaction equation

HRID 2182619 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]23[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[C:21]([Cl:23])[N:20]=[C:19]([Cl:24])[CH:18]=4)[C:13](=[O:25])[N:12]2[NH:11][CH2:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:37](Cl)([CH3:39])=[O:38].O>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]23[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[C:21]([Cl:23])[N:20]=[C:19]([Cl:24])[CH:18]=4)[C:13](=[O:25])[N:12]2[N:11]([C:37](=[O:38])[CH3:39])[CH2:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 22479146HCID 22479146, compound

Product 1

HCID 22479271HCID 22479271, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound from Example 100 (80 mg) in dry THF (2 mL) under N2 was added DIEA (0.073 mL) followed by AcCl (0.024 mL) and the reaction mixture stir-red at room temperature for 18 hours. Water (10 mL) and EtOAc (10 mL) were added and the mixture was shaken. The aqueous phase was then separated and extracted with EtOAc. The combined organics were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by chromatography (silica gel; EtOAc/hexanes; chromatotron) to give the titled compound (71 mg). MS (m/z) 513 (MH+); mp. 91° C.

Workup

  1. customThe aqueous phase was then separated
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (silica gel; EtOAc/hexanes; chromatotron)

Sources & evidence

ORD record
ord-79d5a9b06a6a4a08bef93593e4146dfc
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

Loading…