Ammonium Chloride → HCID 9841742, compound

HRID 276103Notes

Reaction equation

HRID 276103 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])=[N:7][CH:6]=1)[CH2:2][CH3:3].CC(C)([O-])C.[K+].Br[CH2:31][CH:32]1[CH2:34][CH2:33]1.[NH4+].[Cl-]>CS(C)=O>[CH:34]1([CH2:33][N:4]([CH2:1][CH2:2][CH3:3])[C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]([C:15]3[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=3[CH3:21])=[N:7][CH:6]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81503BromomethylcyclopropaneHCID 9944316HCID 9944316, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 9841742HCID 9841742, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the product of step E (72 mg, 9.24 mmol) in DMSO (0.7 mL) was added potassium t-butoxide (40 mg, 0.36 mmol), followed by slow dropwise addition of bromomethylcyclopropane (0.028 mL, 0.3 mmol). The mixture was stirred at room temperature for 1 h, diluted by aqueous NH4Cl, and extracted twice with 50% ethyl ether in hexane. Combined organics were dried over Na2SO4, filtered, concentrated, and chromatographed on silica gel (6% to 10% ethyl acetate in hexane) to give 62 mg of the title compound as an oil 1H NMR (CDCl3): δ0.10 (m, 2H), 0.50 (m,2H), 0.78 (t,3H), 1.00 (m, 1H), 1.50 (q,2H), 186 (s, 6H), 2.38 (s, 3H), 2.45 (d, 2H), 2.56 (t, 2H), 4.07 (s, 2H), 6.98 (s, 2H), 7.42 (5, 1H), 7.52 (d,1H), 7.66 (t, 1H), 8.48 (d, 1H), 8.53 (s 1H)ppm.

Workup

  1. extractionextracted twice with 50% ethyl ether in hexane
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel (6% to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6193e4d048a84c8f9d62c339a72e5220
Source dataset
uspto-grants-2002_03
Patent number
US06353103B1

Reaction notes

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