Citric Acid → 4-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid

HRID 1516442Notes

Reaction equation

HRID 1516442 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]([Br:28])[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.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCO.O>[Br: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[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)[N:18]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 686055994-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 674356194-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acidYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[4-(4-bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexane-carboxylic acid ethyl ester (5.8 g) and LiOH.H2O (1.65 g) in THF (100 mL), EtOH (40 mL) and H2O (30 mL) was stirred at RT overnight. The reaction mixture was then acidified with citric acid (7.54 g in 20 mL H2O), and stirred at RT for 1 h. The precipitate was filtered, washed with water, then Et2O, and dried to provide 4-[4-(4-bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid (5.27 g, 97%) as a white powder.

Workup

  1. stirringstirred at RT for 1 h
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. dry with materialEt2O, and dried

Sources & evidence

ORD record
ord-67f8480cacb843d6971463a77acdfadd
Source dataset
uspto-grants-2012_07
Patent number
US08227478B2

Reaction notes

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