HCID 73603366, compound → HCID 86713189, compound

HRID 1500301Notes

Reaction equation

HRID 1500301 reaction equation
[O:1]=[S:2]1(=[O:29])[CH:5]=[C:4]([C:6]2[N:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([C@@H:18]([OH:28])[C@H:19]([NH:22][C:23](=[O:27])[CH:24]([F:26])[F:25])[CH2:20][F:21])=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3]1>C(O)C.[Pd]>[O:29]=[S:2]1(=[O:1])[CH2:3][CH:4]([C:6]2[N:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([C@@H:18]([OH:28])[C@H:19]([NH:22][C:23](=[O:27])[CH:24]([F:26])[F:25])[CH2:20][F:21])=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:5]1

Participants

4

Reactant 1

HCID 73603366HCID 73603366, compound

Product 1

HCID 86713189HCID 86713189, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of the product of step 6, Example 18 (0.042 g, 0.099 mmol, 1 eq) in ethanol (10 mL) is added palladium on carbon (0.010 g, 10% w/w). Resulting reaction mixture is stirred at room temperature for 16 hours. After completion of the reaction, reaction mixture is filtered through celite bed and filtrate is concentrated in vacuo. The crude compound is purified by preparative TLC using 50% ethyl acetate in hexane to afford desired compound (0.010 g) which is washed with n-pentane (3×5 mL) and dried to afford title compound (0.006 g): 1H-NMR (400 MHz, DMSO) δ: 4.03-4.07 (m, 1H), 4.29-4.31 (m, 2H), 4.45-4.57 (m, 5H), 4.64-4.68 (m, 1H), 4.88-4.90 (m, 1H), 5.92 (d, 1H, J=4.16 Hz), 6.20 (t, 1H, J=53.72 Hz), 7.46 (d, 2H, J=8.28 Hz), 7.53 (d, 1H, J=8.08 Hz), 7.71 (d, 2H, J=8.4 Hz), 8.08-8.11 (dd, 1H, J1=8.2 Hz, J2=2.4 Hz), 8.86 (d, 1H, J=8.64 Hz). 8.93 (d, 1H, J=2.36 Hz). LCMS (m/z): [M+H] 428.9.

Workup

  1. customResulting
  2. customreaction mixture
  3. customAfter completion of the reaction, reaction mixture
  4. filtrationis filtered through celite bed and filtrate
  5. concentrationis concentrated in vacuo
  6. customThe crude compound is purified by preparative TLC

Sources & evidence

ORD record
ord-3a54dd19b85242b2a9d4aa0305ecc709
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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