Hydrochloric Acid → HCID 59411313, compound

HRID 1366257Notes

Reaction equation

HRID 1366257 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11](=[O:31])[N:10]2[CH2:32][C:33]2[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([O:43]CC)=[O:42])=[CH:35][CH:34]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[N:10]([CH2:32][C:33]3[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42])=[CH:35][CH:34]=3)[C:11](=[O:31])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:30])[F:29])[CH:22]=3)[C:13]([CH3:20])=[C:14]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59411309HCID 59411309, compound

Product 1

HCID 59411313HCID 59411313, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of ethyl 4-(4-cyanophenyl)-3-{4-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]benzyl}-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate (Example 40) (100 mg, 0.16 mmol) in ethanol (2 ml) is treated with 10% aq. sodium hydroxide solution (3 ml). After 30 minutes at room temperature, the pH of the solution is adjusted to 2 with 1 N hydrochloric acid, and the crude product is extracted with ethyl acetate (3×150 ml). The combined organic phases are washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 10:90→90:10).

Workup

  1. extractionthe crude product is extracted with ethyl acetate (3×150 ml)
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 10:90→90:10)

Sources & evidence

ORD record
ord-a1864b9208ac4136a2bf199b330ce76c
Source dataset
uspto-grants-2011_02
Patent number
US07893073B2

Reaction notes

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