HCID 25142701, compound → HCID 25142825, compound

HRID 1677037Notes

Reaction equation

HRID 1677037 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([N:17]2[CH2:37][CH2:36][C:20]3[NH:21][C:22]4[C:23]([O:28]CC5C=CC=CC=5)=[CH:24][CH:25]=[CH:26][C:27]=4[C:19]=3[CH2:18]2)=[O:16])=[O:8])[CH2:5][CH2:4]1)#[N:2]>C(OCC)(=O)C.[Pd]>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([N:17]2[CH2:37][CH2:36][C:20]3[NH:21][C:22]4[C:23]([OH:28])=[CH:24][CH:25]=[CH:26][C:27]=4[C:19]=3[CH2:18]2)=[O:16])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 1

HCID 25142701HCID 25142701, compound

Product 1

HCID 25142825HCID 25142825, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The (1R,2R)-2-(6-Benzyloxy-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carbonyl)-cyclohexanecarboxylic acid (1-cyano-cyclopropyl)-amide in ethyl acetate (15 mL) was hydrogenated over 5% palladium on carbon (10 mg). After an apparent uptake of 5 mL (30 min) the reaction was stopped and a sample taken for LCMS. The catalyst was filtered off and a different batch of catalyst and ethanol (5 mL) were added and the hydrogenation continued. Although there was no further uptake apparent after 3 h the reaction was stopped and LCMS indicated that the reduction had proceeded to the required product. Purified by preparative HPLC (0.5% HCOOH, CH3CN/H2O gradient) to give a white powder (34.7 mg, 43%)

Workup

  1. customAfter an apparent uptake of 5 mL (30 min)
  2. filtrationThe catalyst was filtered off
  3. additiona different batch of catalyst and ethanol (5 mL) were added
  4. customapparent after 3 h
  5. customPurified by preparative HPLC (0.5% HCOOH, CH3CN/H2O gradient)

Sources & evidence

ORD record
ord-5df6b614d38148669b1d53fc6ac09b3f
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

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