Ethanol → 4-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclo-hexanecarboxylic acid

HRID 1947047Notes

Reaction equation

HRID 1947047 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:27]4[C:22](=[C:23]([O:28][CH2:29][CH2:30][CH2:31][S:32](=[O:35])(=[O:34])[NH2:33])[CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O.O.CCO>C1COCC1>[S:32]([CH2:31][CH2:30][CH2:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:22]=1[CH:21]=[CH:20][N:19]2[C:17]1[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)[N:18]=1)(=[O:35])(=[O:34])[NH2:33]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 597434464-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 693071564-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclo-hexanecarboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexane-carboxylic acid ethyl ester (590 mg, 1.176 mmol) and LiOH.H2O (493.5 mg, 11.76 mmol) were combined in THF (2.5 mL), H2O (2.5 mL), and EtOH (2.0 mL) and allowed to stir overnight at RT. 10% HV1 solution was then added and the product precipitated. The organic solvents were removed in vacuo and the remaining suspension was filtered, washed with water and the yellow solid dried to yield 4-{4-[4-(3-sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclo-hexanecarboxylic acid (Compound 220, 550 mg, 99%).

Workup

  1. addition10% HV1 solution was then added
  2. customthe product precipitated
  3. customThe organic solvents were removed in vacuo
  4. filtrationthe remaining suspension was filtered
  5. washwashed with water
  6. customthe yellow solid dried

Sources & evidence

ORD record
ord-ba47d25974ce4a43a50b7800f532ca9c
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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