HCID 178471577, compound → HCID 178471578, compound

HRID 2350907Notes

Reaction equation

HRID 2350907 reaction equation
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:49])[C:11]2[CH:17]=[C:16]([CH2:18][N:19]([CH2:26][C:27]3[CH:48]=[CH:47][C:30]([C:31]([NH:33][C@H:34]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:32])=[CH:29][CH:28]=3)[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>C(O)(=O)C.[Pt]=O>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:49])[C:11]2[CH2:17][CH:16]([CH2:18][N:19]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:31]([NH:33][C@H:34]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:32])=[CH:47][CH:48]=3)[C:20](=[O:25])[C:21]([F:23])([F:24])[F:22])[CH2:15][NH:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:4])([CH3:3])[CH3:5]

Participants

4

Reactant 1

HCID 178471577HCID 178471577, compound2×

Product 1

HCID 178471578HCID 178471578, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

To 3.75 g. (5.43 mmol) of the product of Example 3, diethyl N-[N-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-ylmethyl)-N-trifluoroacetyl-4-aminomethylbenzoyl]-glutamate, in 60 mL of glacial acetic acid are added 575 mg of platinum oxide. The suspension was hydrogenated in a Parr apparatus at 50 psi at 25° C. for 3 h. The reaction mixture was filtered through Celite and the solvent removed under reduced pressure. The residue was taken up in methylene chloride and extracted twice with a saturated solution of sodium bicarbonate and the organic layers dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed, eluting with 5% methanol in methylene chloride to give 1.25 g (33% yield) of diethyl N-[N-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-N-trifluoroacetyl-4-aminomethylbenzoyl)-glutamate; 1H NMR (Me2SO d6) delta 1.11-1.15 (m, 6H), 1.33 (s, 9H), 1.6-2.1 (m, 6H), 2.28-2.33 (m, 2H), 3.07-3.18 (m, 1H), 3.97-4.10 (m, 4H), 4.10-4.20 (m, 1H), 6.64-6.67 (m, 1H), 8.03-8.06, (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent removed under reduced pressure
  3. extractionextracted twice with a saturated solution of sodium bicarbonate
  4. dry with materialthe organic layers dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed
  7. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-ce95863680ec438aac1c84d8cf235386
Source dataset
uspto-grants-1989_10
Patent number
US04871746

Reaction notes

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