HCID 44224224, compound → HCID 44468572, compound

HRID 1615850Notes

Reaction equation

HRID 1615850 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH3:41])[N:18]([CH2:19]/[CH:20]=[CH:21]/[C:22]3[CH:23]=[C:24]4[C:37](=[CH:38][CH:39]=3)[CH2:36][C:26]3([C:34]5[C:29](=[N:30][CH:31]=[CH:32][CH:33]=5)[NH:28][C:27]3=[O:35])[CH2:25]4)[C:17](=[O:40])[C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1>CO.[Pd]>[F:8][C:6]1[CH:5]=[C:4]([C@@:9]2([CH3:41])[N:18]([CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[C:24]4[C:37](=[CH:38][CH:39]=3)[CH2:36][C@:26]3([C:34]5[C:29](=[N:30][CH:31]=[CH:32][CH:33]=5)[NH:28][C:27]3=[O:35])[CH2:25]4)[C:17](=[O:40])[C:12]3([CH2:13][CH2:14][CH2:15][CH2:16]3)[NH:11][CH2:10]2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 44224224HCID 44224224, compound

Product 1

HCID 44468572HCID 44468572, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-{(1E)-3-[(8R)-8-(3,5-difluorophenyl)-8-methyl-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]prop-1-en-1-yl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (the first eluting peak of Example 1) (32 mg, 0.058 mmol) was dissolved in 1 mL of methanol and hydrogenated using an H-Cube apparatus and 10% Palladium on carbon cartridge while eluting with 10% acetic acid in methanol. The reaction was concentrated in vacuo and partitioned between ethyl acetate and 10% sodium bicarbonate. The layers were separated. The organic layer was washed with brine, dried over sodium sulfate, filtered and conc in vacuo to yield the title compound MS: m/z=557 (M+1), HRMS: m/z=557.2713 (M+1); calculated m/z=557.2723 (M+1) for C33H35F2N4O2.

Workup

  1. washwhile eluting with 10% acetic acid in methanol
  2. concentrationThe reaction was concentrated in vacuo
  3. custompartitioned between ethyl acetate and 10% sodium bicarbonate
  4. customThe layers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered and conc in vacuo

Sources & evidence

ORD record
ord-31adcc20eabf4eb7bb11a1f61124af78
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

Loading…