Acetic Anhydride → HCID 86607086, compound

HRID 1594495Notes

Reaction equation

HRID 1594495 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH2:15][CH2:16][CH2:17][NH:18][C:19]1[C:24]([C:25]2[N:30]=[CH:29][N:28]=[C:27]([O:31][C:32]3[C:37]4[N:38]=[C:39]([NH2:41])[S:40][C:36]=4[CH:35]=[CH:34][CH:33]=3)[CH:26]=2)=[CH:23][CH:22]=[C:21]([C:42]([F:45])([F:44])[F:43])[N:20]=1.C(=O)([O-])[O-].[K+].[K+].[C:52](OC(=O)C)(=[O:54])[CH3:53]>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH2:15][CH2:16][CH2:17][NH:18][C:19]1[C:24]([C:25]2[N:30]=[CH:29][N:28]=[C:27]([O:31][C:32]3[C:37]4[N:38]=[C:39]([NH:41][C:52](=[O:54])[CH3:53])[S:40][C:36]=4[CH:35]=[CH:34][CH:33]=3)[CH:26]=2)=[CH:23][CH:22]=[C:21]([C:42]([F:45])([F:43])[F:44])[N:20]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 86607087HCID 86607087, compound

Product 1

HCID 86607086HCID 86607086, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(6-(2-(3-(2-methylpiperidin-1-yl)propylamino)-6-(trifluoromethyl)pyridin-3-yl)pyrimidin-4-yloxy)benzo [d]thiazol-2-amine trifluoroacetic acid salt, Example 80, (29 mg, 0.052 mmol), potassium carbonate (35 mg, 0.253 mmol) and acetic anhydride (2 mL) was heated at 90° C. in a microwave synthesizer for 10 min. to give MS (ESI, pos. ion.) m/z: 658 (M+1). The reaction mixture was dissolved in DCM (10 mL), filtered, and concentrated in vacuo. The residue was purified by reverse phase HPLC (Phenomenex Prodigy 5μ ODS-3 100 Å column, gradient: 20-100% CH3CN (0.1% TFA)/H2O (0.1% TFA) over 15 min) to give the title compound as a light-yellow amorphous solid. MS (ESI, pos. ion.) m/z: 700 (M+1).

Workup

  1. customto give MS (ESI, pos. ion.) m/z
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by reverse phase HPLC (Phenomenex Prodigy 5μ ODS-3 100 Å column, gradient: 20-100% CH3CN (0.1% TFA)/H2O (0.1% TFA) over 15 min)

Sources & evidence

ORD record
ord-e92e950e264f4fc4aafbec86e29670f0
Source dataset
uspto-grants-2007_11
Patent number
US07301022B2

Reaction notes

Loading…