(3,5-bis-trifluoromethyl-benzyl)-[6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-ylmethyl]-carbamic acid methyl ester → [(3,5-Bis-trifluoromethyl-benzyl)-(2-pentyl-quinolin-3-ylmethyl)-amino]-acetic acid tert-butyl ester

HRID 577786Notes

Reaction equation

HRID 577786 reaction equation
COC(=O)N(CC1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)CC1C=C2C(C)=NN(C)C2=NC=1N(CC1CCCC1)CC.[C:42]([O:46][C:47](=[O:81])[CH2:48][N:49]([CH2:66][C:67]1[CH:72]=[C:71]([C:73]([F:76])([F:75])[F:74])[CH:70]=[C:69]([C:77]([F:80])([F:79])[F:78])[CH:68]=1)[CH2:50][C:51]1[C:52]([C:61]#[C:62][CH2:63][CH2:64][CH3:65])=[N:53][C:54]2[C:59]([CH:60]=1)=[CH:58][CH:57]=[CH:56][CH:55]=2)([CH3:45])([CH3:44])[CH3:43]>C(O)C.[Pd]>[C:42]([O:46][C:47](=[O:81])[CH2:48][N:49]([CH2:66][C:67]1[CH:72]=[C:71]([C:73]([F:76])([F:75])[F:74])[CH:70]=[C:69]([C:77]([F:78])([F:79])[F:80])[CH:68]=1)[CH2:50][C:51]1[C:52]([CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])=[N:53][C:54]2[C:59]([CH:60]=1)=[CH:58][CH:57]=[CH:56][CH:55]=2)([CH3:43])([CH3:44])[CH3:45]

Participants

5

Reactant 2

HCID 11671498(3,5-bis-trifluoromethyl-benzyl)-[6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-ylmethyl]-carbamic acid methyl esterHCID 57486794[(3,5-Bis-trifluoromethyl-benzyl)-(2-pent-1-ynyl-quinolin-3-ylmethyl)-amino]-acetic acid tert-butyl ester

Product 1

HCID 57473632[(3,5-Bis-trifluoromethyl-benzyl)-(2-pentyl-quinolin-3-ylmethyl)-amino]-acetic acid tert-butyl esterYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

The compound obtained in Example 16, [(3,5-bis-trifluoromethyl-benzyl)-(2-pent-1-ynyl-quinolin-3-ylmethyl)-amino]-acetic acid tert-butyl ester (163 mg, 0.3 mmol) was dissolved in ethanol (3 mL), and palladium [10% on carbon powder (50 mg)] was added. The resulting mixture was stirred under H2 (using a balloon) for 3 h. The sample was diluted in ethanol and filtered through Celite™. The Celite™ was washed with ethanol, the filtrate was concentrated by rotary evaporation, and the resulting sample was dried overnight under vacuum and the crude was purified (Biotage Horizon HPFC chromatography system, SiO2, 80:20 hexanes:ethyl acetate) to give the titled product as a colorless oil (75 mg), yield: 45%, of 96.3% purity (HPLC: Inertsil ODS-3V C18, 20:80 [KH2PO4 (0.01M, pH 3.2):CH3CN], 264 nm, Rt 49.0 min)

Workup

  1. customfor 3 h
  2. filtrationfiltered through Celite™
  3. washThe Celite™ was washed with ethanol
  4. concentrationthe filtrate was concentrated by rotary evaporation
  5. customthe resulting sample was dried overnight under vacuum
  6. customthe crude was purified (Biotage Horizon HPFC chromatography system, SiO2, 80:20 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-39a3b08fea5b45f98c9f6c30c9d09972
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

Loading…