Hydrochloric Acid → HCID 58557318, compound

HRID 1969863Notes

Reaction equation

HRID 1969863 reaction equation
O1CCO[CH:2]1[CH2:6][CH2:7][C:8]1[CH:13]=[N:12][C:11]2[N:14]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:15]=[CH:16][C:10]=2[C:9]=1[NH:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.Cl.[BH4-].[Na+]>CCO>[CH:28]1([N:27]2[C:9]3[C:8](=[CH:13][N:12]=[C:11]4[N:14]([S:17]([C:20]5[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=5)(=[O:19])=[O:18])[CH:15]=[CH:16][C:10]4=3)[CH2:7][CH2:6][CH2:2]2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 58557742HCID 58557742, compound

Product 1

HCID 58557318HCID 58557318, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-(2-(1,3-dioxolan-2-yl)ethyl)-N-cyclohexyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-amine (0.209 g, 0.445 mmol) in EtOH (2 mL) was added aqueous HCl (12 N, 0.186 mL, 2.23 mmol) dropwise. The mixture was heated at about 40° C. for about 2 h and then cooled to about 0° C. in an ice bath. Sodium borohydride (0.118 g, 3.12 mmol) was added portionwise and the mixture was warmed to ambient temperature. After about 2 h the solvent was removed under reduced pressure and the residue was partitioned between EtOAc and saturated aqueous NaHCO3 (10 mL each). The aqueous phase was extracted with EtOAc (2×5 mL) and the combined organics were washed with water and brine (5 mL each), dried over anhydrous Na2SO4, filtered and concd under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-50% EtOAc in heptane to give 1-cyclohexyl-7-tosyl-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-h]-[1,6]naphthyridine (0.138 g, 75%) as a white solid: LC/MS (Table 1, Method b) Rt=3.01 min; MS m/z: 410 (M+H)+.

Workup

  1. temperaturecooled to about 0° C. in an ice bath
  2. temperaturethe mixture was warmed to ambient temperature
  3. customAfter about 2 h the solvent was removed under reduced pressure
  4. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3 (10 mL each)
  5. extractionThe aqueous phase was extracted with EtOAc (2×5 mL)
  6. washthe combined organics were washed with water and brine (5 mL each)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 0-50% EtOAc in heptane

Sources & evidence

ORD record
ord-974c553a3a0042c898391b80bb4fe4a3
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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