Acetic Acid → HCID 118417117、化合物

HRID 1483046ノート

反応式

HRID 1483046 の反応式
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:12][CH2:13][NH:14][C:15](=O)OC(C)(C)C.FC(F)(F)C(O)=O.[F:29][C:30]([F:46])([F:45])[C@@H:31]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[C:32]1[CH:37]=[CH:36][C:35](C=O)=[CH:34][CH:33]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:65]>C(Cl)Cl.CO>[ClH:65].[F:46][C:30]([F:29])([F:45])[C@@H:31]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[C:32]1[CH:33]=[CH:34][C:35]([CH2:15][NH:14][CH2:13][CH2:12][N:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]2=[O:1])=[CH:36][CH:37]=1

参加物

9

反応物 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 86691246HCID 86691246、化合物HCID 90135616HCID 90135616、化合物

生成物 1

HCID 118417117HCID 118417117、化合物収率 4.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

Dissolve tert-butyl 2-(1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)ethylcarbamate (220 mg, 0.76 mmol) in DCM (3 mL) and add trifluoroacetic acid (1 mL, 13.23 mmol). Stir at ambient temperature for 30 minutes. Concentrate the mixture under reduced pressure, then dissolve in 1,2-dichloroethane (20 mL). Add N-[(1S)-2,2,2-trifluoro-1-(4-formylphenyl)-ethyl]-methanesulfonamide (150 mg, 0.53 mmol), acetic acid (0.05 mL, 0.87 mmol), and sodium triacetoxyborohydride (642.3 mg, 3.03 mmol). Stir the mixture at ambient temperature overnight. Concentrate under reduced pressure to give a residue and dilute the residue with MeOH (2 mL). Purify the residue via preparatory TLC using 10% MeOH in DCM to give a colorless oil. Dissolve the oil in MeOH (3 mL) and add HCl (1M in diethyl ether; 0.5 mL, 0.5 mmol) and stir for 30 minutes. Concentrate under reduced pressure to give the title compound as a white solid (10 mg, 3.7%). MS (m/z): 456 (M-Cl).

後処理

  1. concentrationConcentrate the mixture under reduced pressure
  2. dissolutiondissolve in 1,2-dichloroethane (20 mL)
  3. stirringStir the mixture at ambient temperature overnight
  4. concentrationConcentrate under reduced pressure
  5. customto give a residue
  6. customPurify the residue via preparatory TLC
  7. customto give a colorless oil
  8. stirringstir for 30 minutes
  9. concentrationConcentrate under reduced pressure

出典と根拠

ORDレコード
ord-43debd9f465440859e30a3aec58f84cc
出典データセット
uspto-grants-2016_08
特許番号
US09416138B2

反応ノート

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