Sodium Bicarbonate → HCID 89457107, compound

HRID 1915778Notes

Reaction equation

HRID 1915778 reaction equation
[F:1][CH:2]([F:27])[CH2:3][N:4]1[C:8]([N:9]2[CH2:15][CH:14](O)[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]2)=[C:7]([N+:24]([O-:26])=[O:25])[CH:6]=[N:5]1.COCCN(S(F)(F)[F:38])CCOC.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1>[F:1][CH:2]([F:27])[CH2:3][N:4]1[C:8]([N:9]2[CH2:15][CH:14]([F:38])[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]2)=[C:7]([N+:24]([O-:26])=[O:25])[CH:6]=[N:5]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 89456848HCID 89456848, compound

Product 1

HCID 89457107HCID 89457107, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(1-(2,2-difluoroethyl)-4-nitro-1H-pyrazol-5-yl)-6-hydroxy-1,4-diazepane-1-carboxylate (370 mg, 0.95 mmol) in DCM (10 mL) was added deoxo-Fluor® (50% solution in THF, 1.0 mL, 2.37 mmol) and the mixture was stirred at room temperature for 18 hr. Saturated aqueous NaHCO3 solution (10 mL) was added slowly and the mixture was stirred for 15 min. The aqueous layer was extracted with DCM (10 mL), the combined organic layers were passed through a phase separation cartridge and the solvent was removed under reduced pressure. Purification via silica gel column chromatography gave tert-butyl 4-(1-(2,2-difluoroethyl)-4-nitro-1H-pyrazol-5-yl)-6-fluoro-1,4-diazepane-1-carboxylate as a pale green gum (366 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 6.34-6.00 (m, 1H), 5.08-2.75 (m, 11H), 1.48 (s, 9H).

Workup

  1. stirringthe mixture was stirred for 15 min
  2. extractionThe aqueous layer was extracted with DCM (10 mL)
  3. customthe combined organic layers were passed through a phase separation cartridge
  4. customthe solvent was removed under reduced pressure
  5. customPurification via silica gel column chromatography

Sources & evidence

ORD record
ord-fed144691d2143449acd80920048388e
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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