HCID 68292749, compound → HCID 68292622, compound

HRID 1504957Notes

Reaction equation

HRID 1504957 reaction equation
C(OC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][C:21]2[N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]=[CH:24][N:25]=2)=[CH:14][CH:13]=1)=O)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][C:21]2[N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]=[CH:24][N:25]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 68292749HCID 68292749, compound

Product 1

HCID 68292622HCID 68292622, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 58 (80 mg, 0.18 mmol) in EtOAc (5 mL) was added Pd/C (10 mg, 10%) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 balloon at room temperature for 2 h. The suspension was filtered and the solid was washed by EtOAc. The filtrates were concentrated to dryness to give compound 59 (38 mg, 70%) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.32-7.43 (m, 1H), 6.96-7.02 (m, 3H), 6.93 (d, 2H, J=8.3 Hz), 3.17 (t, 2H, J=7.4 Hz), 2.66 (t, 2H, J=7.4 Hz), 2.05-2.13 (m, 2H), 1.62 (s, 9H).

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with H2 several times
  3. filtrationThe suspension was filtered
  4. washthe solid was washed by EtOAc
  5. concentrationThe filtrates were concentrated to dryness

Sources & evidence

ORD record
ord-99c7aec393ee45258e63aa312505a010
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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