HCID 178520451, compound → HCID 178512831, compound

HRID 1783443Notes

Reaction equation

HRID 1783443 reaction equation
C1(CCC(/[N:11]=[C:12](/[NH:41]C(=O)CCC2C=CC=CC=2)\[NH:13][CH2:14][CH2:15][CH2:16][C@H:17]2[C:20](=[O:21])[N:19]([C:22](=[O:30])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:18]2[C:31]([O:33]CC2C=CC=CC=2)=[O:32])=O)C=CC=CC=1>C1COCC1.Cl.[Pd]>[NH:13]([CH2:14][CH2:15][CH2:16][C@H:17]1[C:20](=[O:21])[N:19]([C:22](=[O:30])[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:18]1[C:31]([OH:33])=[O:32])[C:12]([NH2:41])=[NH:11]

Participants

5

Reactant 1

HCID 178520451HCID 178520451, compound

Product 1

HCID 178512831HCID 178512831, compoundYield 10.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 150 (10 mg, 1.0 eq.) in THF (3 mL) and 1N HCl (0.5 mL) was added 10% Pd/C (20 mg). The reaction flask was then evacuated and flushed with hydrogen and stirred under an atmosphere of hydrogen for 18 hours. The reaction was then filtered through Celite and concentrated in vacuo. The crude material was purified via HPLC (C18, acetonitrile/water, 0.1% TFA) to yield 151 (0.5 mg).

Workup

  1. customThe reaction flask was then evacuated
  2. customflushed with hydrogen
  3. filtrationThe reaction was then filtered through Celite
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified via HPLC (C18, acetonitrile/water, 0.1% TFA)

Sources & evidence

ORD record
ord-f39051919455464f8b3b64569b064009
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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