HCID 18448528, compound → HCID 69431308, compound

HRID 1269464Notes

Reaction equation

HRID 1269464 reaction equation
[N:1]1([CH2:7][C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([NH:20][C:21](=[O:42])[CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][N:24]2[S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)(=[O:31])=[O:30])[CH2:15][CH2:14][CH2:13]3)=[CH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCO>[CH3:9][C@@H:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C@H:16]([NH:20][C:21](=[O:42])[CH2:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][N:24]1[S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:41])[F:39])[CH:33]=1)(=[O:31])=[O:30])[CH2:15][CH2:14][CH2:13]2)[CH2:7][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 18448528HCID 18448528, compound

Product 1

HCID 69431308HCID 69431308, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[6-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-2-yl]-acetamide (34 mg, 0.05 mmol), EtOH (2 mL), Pd/Al2O3 (Johnson Matthey, 12 mg, 0.1 eq) was purged with H2 and connected to a H2 balloon for 30 min at RT. The catalyst was filtered through Celite and washed with MeOH. The filtrate was concentrated in vacuo. The crude was purified by silica gel chromatography (7%–10% MeOH—CH2Cl2) to afford the title compound as a mixture of two diastereomers. MS (ESI): 606 (M+H)+. Calc'd for C32H42F3N3O3S—605.29.

Workup

  1. customwas purged with H2
  2. filtrationThe catalyst was filtered through Celite
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe crude was purified by silica gel chromatography (7%–10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-c17da065b3424feb896129c29e10fce1
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

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