Water → HCID 68997739, compound

HRID 1821428Notes

Reaction equation

HRID 1821428 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]2)[CH:5]=[CH:6][C:7]=1/[CH:8]=[CH:9]/[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][N:11]=1.[C:28]1(=O)[O:33][C:31](=[O:32])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.C(N(CC)CC)C.O>CC1C=CC(C)=CC=1>[OH:27][CH2:26][CH2:25][N:22]1[CH2:21][CH2:20][N:19]([C:4]2[CH:5]=[CH:6][C:7](/[CH:8]=[CH:9]/[C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][N:11]=3)=[C:2]([N:1]3[C:31](=[O:32])[C:30]4[C:29](=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:28]3=[O:33])[CH:3]=2)[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 69004339HCID 69004339, compound

Product 1

HCID 68997739HCID 68997739, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

(E)-2-(4-{3-amino-4-[2-(1H-indazol-3-yl)vinyl]phenyl}piperazin-1-yl)ethanol (0.10 g, 0.28 mmol) obtained in Step 3 of Example 273 was dissolved in p-xylene (3.5 mL) and the solution was added with phthalic anhydride (49 mg, 0.33 mmol), triethylamine (0.02 mL, 0.14 mmol), molecular sieves 3A (0.10 g), followed by stirring at 140° C. for 25 hours. The solution was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The filtrate was reslurried with ethyl acetate to obtain Compound 299 (4.5 mg, 3%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-63e1a346f808435db4b2dd4a5b5bda36
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…