HCID 70980249, compound → HCID 70980412, compound

HRID 1749087Notes

Reaction equation

HRID 1749087 reaction equation
C[O:2][C:3](=O)[C@@H:4]([NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[C:9]([NH:16][C:17](=[O:29])[C@@H:18]([N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH3:21])[CH3:19])[N:8]=1)[CH3:5]>C1COCC1.C(O)(=O)C.CO.[Pd]>[C:25]([O:24][C:22](=[O:23])[N:20]([CH3:21])[C@H:18]([C:17](=[O:29])[NH:16][C:9]1[CH:10]=[CH:11][C:12]2[NH:13][C:3](=[O:2])[C@H:4]([CH3:5])[NH:6][C:7]=2[N:8]=1)[CH3:19])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 1

HCID 70980249HCID 70980249, compound

Product 1

HCID 70980412HCID 70980412, compoundYield 43.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-{6-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-nitro-pyridin-2-ylamino}-propionic acid methyl ester (90 mg, 0.21 mmol) in THF (3 mL) and acetic acid (3 mL) and MeOH (3 mL) was added Pd/C (10%, 90 mg) and the reaction mixture was hydrogenated for 3 h. The catalyst was filtered and the filtrate evaporated. The residue was partitioned between saturated NaHCO3 and EtOAc. The organic phase was dried (MgSO4), filtered and evaporated. The crude material was purified by preparative HPLC to afford methyl-[(S)-1-((S)-3-methyl-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-b]pyrazin-6-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (33 mg). MS: [M+H]+=364.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between saturated NaHCO3 and EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-17b5b41237b94dacbd3ca33c48e83f47
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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