(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 577786ノート

反応式

HRID 577786 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-39a3b08fea5b45f98c9f6c30c9d09972
出典データセット
uspto-grants-2015_05
特許番号
US09040558B2

反応ノート

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