HCID 67282662, compound → HCID 67281391, compound

HRID 446972Notes

Reaction equation

HRID 446972 reaction equation
C(O[C:9](=O)[N:10]([CH:12]([C:14](=[O:48])[NH:15][CH:16]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[C:17]([N:19]1[CH2:23][CH2:22][CH:21]2[N:24]([S:38]([CH3:41])(=[O:40])=[O:39])[CH2:25][CH:26]([C:27](=[O:37])[NH:28][CH:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:30])[CH:20]12)=[O:18])[CH3:13])C)C1C=CC=CC=1>CO.C(#N)C.O.[Pd]>[C:31]1([CH:29]([NH:28][C:27]([CH:26]2[CH2:25][N:24]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:21]3[CH2:22][CH2:23][N:19]([C:17](=[O:18])[CH:16]([CH:42]4[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]4)[NH:15][C:14](=[O:48])[CH:12]([NH:10][CH3:9])[CH3:13])[CH:20]23)=[O:37])[CH3:30])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 1

HCID 67282662HCID 67282662, compound

Product 1

HCID 67281391HCID 67281391, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of 32 (113 mg, 0.16 mmol) in MeOH (15 mL) was treated with 10% Pd/C (wet, 151 mg) and pressurized under H2 atmosphere (50 psi) using a Parr apparatus. After 2.5 h, the reaction mixture was filtered through a filter disc (Acrodisc-PSF-0.45 μM) and rinsed with MeOH. The filtrate was concentrated to afford the crude amine 33 which was diluted with ACN/H2O containing 0.1% HOAc and purified by reverse phase HPLC (2″ Dynamax® C18, 10% ACN/H2O to 100% ACN over 30 min). The product-containing fractions were combined, frozen, and lyophilized to afford 33 as a white solid.

Workup

  1. filtrationthe reaction mixture was filtered through a filter disc (Acrodisc-PSF-0.45 μM)
  2. washrinsed with MeOH
  3. concentrationThe filtrate was concentrated
  4. customto afford the crude amine 33 which
  5. custompurified by reverse phase HPLC (2″ Dynamax® C18, 10% ACN/H2O to 100% ACN over 30 min)
  6. temperaturefrozen

Sources & evidence

ORD record
ord-0fa54716407442a0900014aa474ef43b
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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