Acetic Acid → HCID 67066703, compound

HRID 571701Notes

Reaction equation

HRID 571701 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][N:18]=[C:19]([N:20]3[CH2:25][CH2:24][CH2:23][C:22](=O)[CH2:21]3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CC(O)=O.[BH3-]C#N.[Na+]>CO.O>[CH2:27]([NH:34][CH:22]1[CH2:23][CH2:24][CH2:25][N:20]([C:19]2[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=4)(=[O:3])=[O:2])[C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:21]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 67066746HCID 67066746, compound

Product 1

HCID 67066703HCID 67066703, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-one (75 mg, 0.2 mmol) and benzylamine (25 μL, 0.22 mmol) in MeOH (3 mL) was added AcOH (20 μL, 0.4 mmol) and NaBH3CN (32 mg, 0.5 mmol). The solution was stirred at rt for 16 hr after which time the solvent was removed in vacuo to afford a residue which was diluted with water and extracted with EtOAc. The organic phase was separated, washed with aq. NaHCO3 and water, dried (Na2SO4) and concentrated in vacuo to afford a residue which was purified by column chromatography (silica gel, gradient EtOAc in hexanes). EIMS (m/z): calcd. for C25H27N5O2S (M++1) 462.2. found 462.2.

Workup

  1. customwas removed in vacuo
  2. customto afford a residue which
  3. extractionextracted with EtOAc
  4. customThe organic phase was separated
  5. washwashed with aq. NaHCO3 and water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto afford a residue which
  9. customwas purified by column chromatography (silica gel, gradient EtOAc in hexanes)

Sources & evidence

ORD record
ord-c5a11dcfde814ee5bf1ff3e44aaba401
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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