Acetic Anhydride → HCID 58691333, compound

HRID 1594467Notes

Reaction equation

HRID 1594467 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16]2[C:21]([C:22]3[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]4[C:34]5[N:35]=[C:36]([NH2:38])[S:37][C:33]=5[CH:32]=[CH:31][CH:30]=4)[CH:23]=3)=[CH:20][CH:19]=[C:18]([C:39]([F:42])([F:41])[F:40])[N:17]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:43](OC(=O)C)(=[O:45])[CH3:44]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16]2[C:21]([C:22]3[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]4[C:34]5[N:35]=[C:36]([NH:38][C:43](=[O:45])[CH3:44])[S:37][C:33]=5[CH:32]=[CH:31][CH:30]=4)[CH:23]=3)=[CH:20][CH:19]=[C:18]([C:39]([F:41])([F:42])[F:40])[N:17]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 58691365HCID 58691365, compound

Product 1

HCID 58691333HCID 58691333, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(6-(2((4-benzylmorpholin-2-yl)methylamino)-6-(trifluoromethyl)pyridin-3-yl)pyrimidin-4-yloxy)benzo[d]thiazol-2-amine, Example 1(c), (110 mg, 0.18 mmol) and DMAP (10 mg, 0.08 mmol, Aldrich) in DCM (8 mL) was added acetic anhydride (90 μL, 0.9 mmol, Aldrich). The mixture was stirred at room temperature for 18 h and evaporated under reduced pressure. The residue was dissolved in EtOAc and the solution was washed with a sat. aqueous solution of NaHCO3, H2O and brine, dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography [2% (2N NH3 in MeOH)/DCM] to give the title compound as a light-yellow solid. MS (ESI, pos. ion.) m/z: 636 (M+1).

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe solution was washed with a sat. aqueous solution of NaHCO3, H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified by silica gel column chromatography [2% (2N NH3 in MeOH)/DCM]

Sources & evidence

ORD record
ord-03e9a840ff2345469e2c4691fd915fe7
Source dataset
uspto-grants-2007_11
Patent number
US07301022B2

Reaction notes

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