Sodium borohydride → HCID 67994748, compound

HRID 2361305Notes

Reaction equation

HRID 2361305 reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([N:23]5[CH2:31][C:30]6[C:25](=[CH:26][C:27](OC)=[CH:28][CH:29]=6)[C:24]5=[O:34])[C:18]=4[CH3:35])=[CH:15][N:14]=[C:13]([C:36]([NH2:38])=[O:37])[C:9]=3[NH:10]2)=[CH:6][CH:5]=1)#[N:2].[Cl:39]C1C=CC(C=O)=C(C=1)C(O)=O.[BH4-].[Na+]>CO>[Cl:39][C:27]1[CH:26]=[C:25]2[C:30]([CH2:31][N:23]([C:19]3[C:18]([CH3:35])=[C:17]([C:16]4[C:8]5[C:7]6[C:11](=[CH:12][C:4]([CH2:3][C:1]#[N:2])=[CH:5][CH:6]=6)[NH:10][C:9]=5[C:13]([C:36]([NH2:38])=[O:37])=[N:14][CH:15]=4)[CH:22]=[CH:21][CH:20]=3)[C:24]2=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 71762095-Chloro-2-formylbenzoic acidHCID 54766566HCID 54766566, compound

Product 1

HCID 67994748HCID 67994748, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(1-aminoxycarbonyl)-7-cyanomethyl)-9H-pyrido[3,4-b]indole-4-yl-2-methylaniline 7 (40 mg, 0.112 mmol), 5-chloro-2-formylbenzoic acid (51.6 mg, 0.28 mmol) and 4 angstrom molecular sieves (0.5 g) in methanol (15 mL) was stirred at RT for 24 h. After that the mixture was cooled to −20° C. and sodium borohydride (29.6 mg, 0.78 mmol) was added and the reaction mixture was allowed to warm up to 10° C. The solvent was removed under reduced pressure, quenched with saturated NH4Cl solution (5 ml) and extracted with EtOAc (2×10 ml). Combined organic extracts were washed with water, brine, dried over Na2SO4 and concentrated. The crude product obtained was purified by silica gel column chromatography eluting with 5% MeOH in CHCl3 to give the desired product (10 mg, 0.019 mmol, 17% yield) as a yellow sticky solid.

Workup

  1. temperatureAfter that the mixture was cooled to −20° C.
  2. temperatureto warm up to 10° C
  3. customThe solvent was removed under reduced pressure
  4. customquenched with saturated NH4Cl solution (5 ml)
  5. extractionextracted with EtOAc (2×10 ml)
  6. washCombined organic extracts were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product obtained
  10. customwas purified by silica gel column chromatography
  11. washeluting with 5% MeOH in CHCl3

Sources & evidence

ORD record
ord-590a715f74314391be4e32cba9a407ea
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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