Hydrochloric Acid → HCID 57761903, compound

HRID 230954Notes

Reaction equation

HRID 230954 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:20][CH2:19]3)[N:15]=[C:14]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[N:13]=2)[CH:7]=1.O.O[Li].O.Cl>C1COCC1.C(O)C>[N:34]1([C:14]2[N:13]=[C:12]([C:8]3[CH:7]=[C:6]([CH2:5][CH2:4][C:3]([OH:40])=[O:2])[CH:11]=[CH:10][CH:9]=3)[CH:17]=[C:16]([N:18]3[CH2:19][CH2:20][N:21]([C:24]4[C:29]([C:30]([F:33])([F:31])[F:32])=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:22][CH2:23]3)[N:15]=2)[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57761814HCID 57761814, compound

Product 1

HCID 57761903HCID 57761903, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 3-(3-{2-morpholin-4-yl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-4-yl}-phenyl)-propionic acid methyl ester in THF, add water dropwise until the cloudiness almost persists. To this mixture add LiOH.H2O (10 equivalents) followed by a small amount of ethanol to achieve heterogeneity. Heat the mixture at 55° C. for 2 hours then concentrate under reduced pressure. Add a small amount of water to the residue followed by 10 equivalents of HCl (3M solution). Adjust the final pH to 4 and collect the off-white solid via filtration. Wash the solid with water and dry to afford the title compound. 1H NMR (DMSO-D6): δ 2.58 (t, 2H), 2.89 (t, 2H), 3.29 (br m, 4H), 3.66 (br m, 4H), 3.72 (br m, 4H), 3.79 (br m, 4H), 6.72 (s, 1H), 7.22 (m, 1H), 7.31-7.37 (m, 2H), 7.95 (m, 2H), 8.09 (d, 1H, J=7.87 Hz), 8.54 (d, 1H, J=3.3 Hz).

Workup

  1. concentrationthen concentrate under reduced pressure
  2. additionAdd a small amount of water to the residue
  3. customcollect the off-white solid
  4. filtrationvia filtration
  5. washWash the solid with water
  6. customdry

Sources & evidence

ORD record
ord-d49d57c697a644fd8c865bcbf82bbb60
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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