HCID 69037164, compound → HCID 11363057, compound

HRID 225796Notes

Reaction equation

HRID 225796 reaction equation
C([CH2:8][NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][C@@H:23]([C:26]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:27]([NH2:29])=[O:28])[CH2:22]2)=[CH:14][CH:13]=1)C1C=CC=CC=1>C(O)(C)C.[Pd]>[CH3:8][NH:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][C@@H:23]([C:26]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:27]([NH2:29])=[O:28])[CH2:22]2)=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 69037164HCID 69037164, compound

Product 1

HCID 11363057HCID 11363057, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A stirred solution of the intermediate from Step E (0.8 g, 1.46 mmol) in isopropanol (100 mL) was flushed with nitrogen gas and then palladium (80 mg; 10 wt. % (dry basis) on activated carbon) was added. The reaction flask was then placed under vacuum and then flushed with hydrogen gas (3 cycles). The reaction mixture was then stirred for 2.5 hours and then was flushed with nitrogen gas, filtered and the solvent removed under reduced pressure. To the residue was added a 1:1 mixture of acetic acid/water (1.0 mL) and this mixture was then chromatographed on reverse-phase silica gel (gradient elution, 10-50% ACN/water) to provide 60 mg of the title compound (6% yield) as a bis(trifluoroacetate) salt. MS m/z: [M+H+] calc'd for C30H37N3O 456.3. Found 456.3. Retention time=3.04 min (10-70% ACN: H2O, reverse phase HPLC).

Workup

  1. customflushed with hydrogen gas (3 cycles)
  2. customwas flushed with nitrogen gas
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. additionTo the residue was added
  6. additiona 1:1 mixture of acetic acid/water (1.0 mL)
  7. customthis mixture was then chromatographed on reverse-phase silica gel (gradient elution, 10-50% ACN/water)

Sources & evidence

ORD record
ord-3b62309ce9ba4fae815c1afb9ae8dd6b
Source dataset
uspto-grants-2009_07
Patent number
US07557126B2

Reaction notes

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