Acetic Anhydride → HCID 10388089, compound

HRID 2055977Notes

Reaction equation

HRID 2055977 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([O:17][C:18]4[C:23]5[N:24]=[C:25]([NH2:27])[S:26][C:22]=5[CH:21]=[CH:20][CH:19]=4)[CH:12]=3)=[CH:10][C:4]=2[O:3]1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:28])[CH2:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([O:17][C:18]4[C:23]5[N:24]=[C:25]([NH:27][C:29](=[O:31])[CH3:30])[S:26][C:22]=5[CH:21]=[CH:20][CH:19]=4)[CH:12]=3)=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21865279HCID 21865279, compound

Product 1

HCID 10388089HCID 10388089, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a 100-mL, round-bottomed flask containing 4-[6-(2,2-dimethyl-2,3-dihydro-benzofuran-6-yl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine, (Example 133(b)), (0.50 g, 1.3 mmol) was added toluene (7 mL) and acetic anhydride (0.40 mL, 3.8 mmol, Aldrich). The reaction mixture was heated at 85° C. for 2 h. The toluene was removed in vacuum and the resulting orange solid was re-dissolved in dichloromethane (125 mL), washed with water (150 mL), dried over Na2SO4 and concentrated in vacuum. The resulting orange solid was suspended in dichloromethane (100 mL), collected by filtration, and dried under vacuum to obtain the title compound as a white solid. Mp: 224-225° C. MS (ESI, pos. ion.) m/z: 433 (M+1).

Workup

  1. customThe toluene was removed in vacuum
  2. dissolutionthe resulting orange solid was re-dissolved in dichloromethane (125 mL)
  3. washwashed with water (150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. filtrationcollected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-1b6bb73f17204526920554391897894b
Source dataset
uspto-grants-2008_02
Patent number
US07332511B2

Reaction notes

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