Sodium Bicarbonate → HCID 86591861, compound

HRID 1815708Notes

Reaction equation

HRID 1815708 reaction equation
[C:1]([NH:5][C:6](=[O:8])[OH:7])([CH3:4])([CH3:3])[CH3:2].[CH:9]1([S:12]([NH2:15])(=[O:14])=[O:13])[CH2:11][CH2:10]1.[Li]CCCC.BrC[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.Br.BrCC1C=CN=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.CCOCC>[N:26]1[CH:27]=[CH:28][C:23]([C:9]2([S:12]([NH2:15])(=[O:14])=[O:13])[CH2:11][CH2:10]2)=[CH:24][CH:25]=1.[C:1]([NH:5][C:6](=[O:7])[O-:8])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 516892Sodium BicarbonateHCID 6427994-(Bromomethyl)pyridine2×HCID 127522194-(Bromomethyl)pyridine hbrHCID 68821921Cyclopropylsulfonylamine tert-butylcarbamateHCID 178418339Butyllithium

Product 1

HCID 86591861HCID 86591861, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

step 47a) To a solution of cyclopropylsulfonylamine tert-butyl carbamate (105 g, 4.52 mmol) in THF (9 mL) cooled to −78° C., was added n-BuLi (6.2 mL, 9.2 mmol, 1.6 M in hexane). The mixture was stirred for 1 h at −78° C., and 0.55 mL (0.5 mmol) of fresh 4-(bromomethyl)pyridine was injected in one portion. The fresh 4-(bromomethyl)-pyridine was made from 4-(bromomethyl)pyridine hydrobromide by tributing between aqueous sodium bicarbonate and ether, ether layer was quickly separated, dried (MgSO4), removed solvent in vacuo, and immediately used to the reaction. The reaction mixture was stirred for 5 min at −78° C., changed the bath into ice water, and stirred for another 1 h. The reaction mixture was diluted with pH 4.0 buffer, adjusted pH to 4, and extracted with EtOAc. The combined extractions were dried (MgSO4), concentrated, and purified by pre-HPLC to afford a mixture (only 0.42 g) with 1-(4-pyridyl)-cyclopropanesulfonamide-tert-butylcarbamate and the mixture was used in next step.

Workup

  1. customwas quickly separated
  2. dry with materialdried (MgSO4)
  3. customremoved solvent in vacuo
  4. customimmediately used to the reaction
  5. stirringThe reaction mixture was stirred for 5 min at −78° C.
  6. stirringstirred for another 1 h
  7. additionThe reaction mixture was diluted with pH 4.0 buffer
  8. extractionextracted with EtOAc
  9. extractionThe combined extractions
  10. dry with materialwere dried (MgSO4)
  11. concentrationconcentrated
  12. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-d7b81fb28b0e439ba2c41fee76b75966
Source dataset
uspto-grants-2005_04
Patent number
US06878722B2

Reaction notes

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