Triethylamine → HCID 70981791, compound

HRID 1749101Notes

Reaction equation

HRID 1749101 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([C@H:9]([C:11](=[O:38])[NH:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:31]3[CH:36]=[CH:35][C:34](Cl)=[CH:33][CH:32]=3)[C:18](=[O:30])[N:19]([C:23]3[CH:28]=[CH:27][C:26](Cl)=[CH:25][CH:24]=3)[CH2:20][C:21]=2[N:22]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CO.[Pd]>[C:1]([O:5][C:6](=[O:39])[N:7]([CH3:8])[C@H:9]([C:11](=[O:38])[NH:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:18](=[O:30])[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:20][C:21]=2[N:22]=1)[CH3:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 89963551HCID 89963551, compound

Product 1

HCID 70981791HCID 70981791, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of {(S)-1-[1,3-bis-(4-chloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (Example 21, product from Step 3) (100 mg, 0.18 mmol) in MeOH (10 mL) were added triethylamine (100 μL, 0.7 mmol, 4 equiv) and Pd/C (10%, 30 mg) and the mixture was hydrogenated overnight. The catalyst was filtered, the filtrate evaporated. The residue was dissolved in EtOAc and washed with H2O. The organic phase was dried (MgSO4), filtered and evaporated. The crude material was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-60%) to afford methyl-[(S)-1-(2-oxo-1,3-diphenyl-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (35 mg). MS: [M+H]+=502.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude material was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-60%)

Sources & evidence

ORD record
ord-c9fd7f25b2324555bab4defdebeb9ca1
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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