Hydrochloric Acid → HCID 59684804, compound

HRID 421804Notes

Reaction equation

HRID 421804 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16]3[O:17][CH:18]=[C:19]([C:21]([O:23]C)=[O:22])[N:20]=3)[C:13](=[O:25])[N:12]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:11]([CH3:36])=[C:10]2[C:37]([CH:39]2[CH2:41][CH2:40]2)=[O:38])=[CH:5][CH:4]=1)#[N:2].[OH-].[Li+].Cl.CO>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[N:14]([CH2:15][C:16]3[O:17][CH:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=3)[C:13](=[O:25])[N:12]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=3)[C:11]([CH3:36])=[C:10]2[C:37]([CH:39]2[CH2:40][CH2:41]2)=[O:38])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 59684873Methyl 2-{[6-(4-cyanophenyl)-5-(cyclopropylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]methyl}-1,3-oxazole-4-carboxylate

Product 1

HCID 59684804HCID 59684804, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-{[6-(4-cyanophenyl)-5-(cyclopropylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]methyl}-1,3-oxazole-4-carboxylate (Example 43) (50 mg, 0.09 mmol) in tetrahydrofuran (1.5 ml) is added a solution of lithium hydroxide (4.24 mg, 0.18 mmol) in water (1.5 ml). The reaction solution is stirred at room temperature overnight (16 h). The pH of the solution is adjusted to less than pH 7 with 1 N hydrochloric acid (500 μl). After 5 minutes stirring, a precipitate is obtained. Methanol (3 ml) is added, and the crude reaction solution is purified directly by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 30:70→90:10). The title compound is isolated as a colourless solid.

Workup

  1. stirringAfter 5 minutes stirring
  2. customa precipitate is obtained
  3. customthe crude reaction solution
  4. customis purified directly by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 30:70→90:10)

Sources & evidence

ORD record
ord-cca7a9bc6347441d8cad673bc28dcf73
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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