Methanol → HCID 66712335, compound

HRID 1262268Notes

Reaction equation

HRID 1262268 reaction equation
C([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:19]2[C:14]([CH:15]=[N:16][C:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)=[CH:23][CH:22]=3)=[N:18]2)=[CH:13][CH:12]=1)C.[OH-].[Li+].CO>O>[CH3:33][N:30]1[CH2:29][CH2:28][N:27]([C:24]2[CH:23]=[CH:22][C:21]([NH:20][C:17]3[N:16]=[CH:15][C:14]4=[CH:13][CH:12]=[C:11]([C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[C:4]([OH:34])=[O:3])[N:19]4[N:18]=3)=[CH:26][CH:25]=2)[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 46851549HCID 46851549, compound

Product 1

HCID 66712335HCID 66712335, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 8-dram vial, 2-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzoic acid ethyl ester (0.250 g, 0.548 mmol), Lithium hydroxide (0.0262 g, 1.10 mmol), Methanol (15 mg), and Water (3.0 mL) were added. The reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuum. The solid was acidified with 1N HCl. The reaction was partitioned DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum to give 2-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzoic acid as a solid (180 mg, 76%). The solid was used as is without further purification.

Workup

  1. customThe solvent was removed under vacuum
  2. customThe reaction was partitioned DCM
  3. customThe organic was separated
  4. washwashed with Brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe solid was filtered
  7. washwashed with DCM
  8. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-c8da005dd9e4460c8d15ca6dbd448912
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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