HCID 86623952, compound → HCID 66998231, compound

HRID 559179Notes

Reaction equation

HRID 559179 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14]2[N:20]([CH3:32])[C:21](=[O:31])[C:22]([C:24]4[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=4)=[CH:23][C:13]3=2)[S:8][CH:9]=1)=[N+]=[N-]>CO.C(O)(=O)C.[Pd]>[NH2:1][CH2:4][C:5]1[N:6]=[C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14]2[N:20]([CH3:32])[C:21](=[O:31])[C:22]([C:24]4[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=4)=[CH:23][C:13]3=2)[S:8][CH:9]=1

Participants

5

Reactant 1

HCID 86623952HCID 86623952, compound

Product 1

HCID 66998231HCID 66998231, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

370 mg (0.73 mmol) of compound B 6-(4-azidomethylthiazol-2-yl)-3-(4-bromophenyl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one are dissolved in 40 ml of methanol and 40 ml of glacial acetic acid. 40 mg of Pd/C are added. The mixture is hydrogenated under 60 psi at 25° C. for 48 hours. The reaction medium is filtered over celite. Washing is carried out with ethanol. The filtrate is evaporated to dryness. The residue is dissolved in a CH2Cl2/MeOH mixture and the product is adsorbed onto silica. Purification is carried out on a silica column, elution being carried out with 97/02/01 CH2Cl2/MeOH/NH4OH and then with 93/05/02 CH2Cl2/MeOH/NH4OH.

Workup

  1. filtrationThe reaction medium is filtered over celite
  2. washWashing
  3. customThe filtrate is evaporated to dryness
  4. dissolutionThe residue is dissolved in a CH2Cl2/MeOH mixture
  5. customPurification
  6. washis carried out on a silica column, elution

Sources & evidence

ORD record
ord-60b93501ce984b31ab43181cf978bfb5
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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