HCID 58560983, compound → HCID 46897030, compound

HRID 2408155Notes

Reaction equation

HRID 2408155 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:37]=[C:38]([Cl:40])[CH:39]=1)[O:7][C@@H:8]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C@@H:9]([C:16]1[CH:29]=[CH:28][C:19]([C:20]([NH:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:21])=[CH:18][CH:17]=1)[CH2:10][CH2:11][C:12]([F:15])([F:14])[F:13])=O>O.C(#N)C.[Pd](Cl)Cl>[Cl:40][C:38]1[CH:37]=[C:6]([CH:5]=[C:4]([C:2]#[N:1])[CH:39]=1)[O:7][C@@H:8]([C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[C@@H:9]([C:16]1[CH:29]=[CH:28][C:19]([C:20]([NH:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:21])=[CH:18][CH:17]=1)[CH2:10][CH2:11][C:12]([F:15])([F:13])[F:14]

Participants

5

Reactant 1

HCID 58560983HCID 58560983, compound

Product 1

HCID 46897030HCID 46897030, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product from Step A (50 mg, 0.087 mmol) in water (0.5 mL) and acetonitrile (0.5 mL) at room temperature was added palladium (II) chloride (1.5 mg, 8.7 μmol). The resulting mixture was stirred at 50° C. for 12 hours. After cooling to room temperature, the mixture was extracted with EtOAc, then the organic layer was filtered through celite. The filtrate was concentrated, then the resulting residue was purified by PTLC eluting with 5% MeOH/DCM+0.1% HOAc to afford the title compound. NMR (500 MHz, CD3OD): δ 7.74 (d, J=8.0 Hz, 2H); 7.36 (d, J=8.0 Hz, 2H); 7.31 (d, J=8.0 Hz, 2H); 7.24 (d, J=9.0 Hz, 2H); 7.22 (s, 1H); 7.12 (s, 1H); 7.09 (s, 1H); 5.64 (d, J=6.5 Hz, 1H); 3.63 (t, J=9.2 Hz, 2H); 3.26-3.23 (m, 1H); 2.62 (t, J=9.5 Hz, 2H); 2.10-2.05 (m, 2H); 2.00-1.95 (m, 2H); LC3 3.59 min. (M+H)+ 579.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. filtrationthe organic layer was filtered through celite
  4. concentrationThe filtrate was concentrated
  5. customthe resulting residue was purified by PTLC
  6. washeluting with 5% MeOH/DCM+0.1% HOAc

Sources & evidence

ORD record
ord-3489ebbf22304ba78a909671f6fc8cee
Source dataset
uspto-grants-2014_08
Patent number
US08809579B2

Reaction notes

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