Sodium Hydroxide → HCID 66997921, compound

HRID 559200Notes

Reaction equation

HRID 559200 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[N:21]([CH3:34])[C:22](=[O:33])[C:23]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=4[Cl:32])=[CH:24][C:14]3=2)[S:9][CH:10]=1)=O)C.[Li+].[BH4-].[OH-].[Na+]>C(Cl)Cl.C1COCC1>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[C:23]1[C:22](=[O:33])[N:21]([CH3:34])[C:15]2[N:16]([CH3:20])[C:17]3[C:13]([C:14]=2[CH:24]=1)=[CH:12][C:11]([C:8]1[S:9][CH:10]=[C:6]([CH2:4][OH:3])[N:7]=1)=[CH:19][CH:18]=3

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 66998161HCID 66998161, compound

Product 1

HCID 66997921HCID 66997921, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution containing 218 mg (0.43 mmol) of compound B, 2-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]thiazole-4-carboxylic acid ethyl ester in 8 ml of CH2Cl2 is refluxed. 430 μl (0.85 mmol) of 2M LiBH4 in THF are added. The mixture is refluxed for 16 h. The reaction medium is left to cool, 10 ml of 1M NaOH are added and the reaction medium is concentrated to dryness. The residue is taken up in H2O, filtered and then washed with H2O and then with MeOH.

Workup

  1. temperatureis refluxed
  2. temperatureThe mixture is refluxed for 16 h
  3. waitThe reaction medium is left
  4. temperatureto cool
  5. concentrationthe reaction medium is concentrated to dryness
  6. filtrationfiltered
  7. washwashed with H2O

Sources & evidence

ORD record
ord-5a32ef2624a04c8b80c1357061b5fd13
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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