Lithium hydroxide, monohydrate → HCID 24998854, compound

HRID 1910840Notes

Reaction equation

HRID 1910840 reaction equation
O.[OH-].[Li+].[O:4]=[C:5]([C:34]1[N:42]2[C:37]([CH:38]=[CH:39][CH:40]=[CH:41]2)=[CH:36][C:35]=1[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([O:27][CH2:28][CH2:29][O:30]C(=O)C)[CH:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)=[O:7]>CO>[OH:30][CH2:29][CH2:28][O:27][C:25]1[CH:24]=[CH:23][N:22]=[C:21]([N:18]2[CH2:19][CH2:20][N:15]([C:12]3[CH:11]=[CH:10][C:9]([NH:8][C:6](=[O:7])[C:5](=[O:4])[C:34]4[N:42]5[C:37]([CH:38]=[CH:39][CH:40]=[CH:41]5)=[CH:36][C:35]=4[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[CH:14][CH:13]=3)[CH2:16][CH2:17]2)[CH:26]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67105825HCID 67105825, compound

Product 1

HCID 24998854HCID 24998854, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium hydroxide monohydrate (0.048 g, 1.16 mmol) was added to a stirred solution of acetic acid 2-[2-(4-{4-[2-oxo-2-(2-phenyl-indolizin-3-yl)-acetylamino]-phenyl}-piperazin-1-yl)-pyridin-4-yloxy]-ethyl ester (0.35 g, 0.58 mmol) in methanol (15 mL) at r.t. under nitrogen and stirred for 3 h. The reaction mixture was evaporated to dryness, diluted with water and extracted with dichloromethane. The organic layer was washed with water and brine solution, dried over sodium sulfate and filtered. The filtrate was concentrated and purified by column chromatography over neutral alumina using 0-1% methanol in dichloromethane to afford N-(4-{4-[4-(2-hydroxy-ethoxy)-pyridin-2-yl]-piperazin-1-yl}-phenyl)-2-oxo-2-(2-phenyl-indolizin-3-yl)-acetamide (0.142 g, 44%) as a yellow solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water and brine solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by column chromatography over neutral alumina using 0-1% methanol in dichloromethane

Sources & evidence

ORD record
ord-a142e385eb7f4e3180348d7f2cad7bd3
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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