Water → HCID 22479271, compound

HRID 1392187Notes

Reaction equation

HRID 1392187 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 stirred 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. stirringthe mixture was shaken
  2. customThe aqueous phase was then separated
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (silica gel; EtOAc/hexanes; chromatotron)

Sources & evidence

ORD record
ord-cf3657a88f204a5aa7e6a9ff1f0e3b62
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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