Ammonium Chloride → HCID 24936969, compound

HRID 218154Notes

Reaction equation

HRID 218154 reaction equation
[C:1]([NH:5][C:6]([NH:8][CH2:9][C:10]([CH3:32])([CH3:31])[CH:11]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[N:19]=[CH:18]2)[CH2:12][CH:13]=[CH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:33]([Zn]CC)C.[NH4+].[Cl-]>ClCCCl>[C:1]([NH:5][C:6]([NH:8][CH2:9][C:10]([CH3:32])([CH3:31])[CH:11]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[N:19]=[CH:18]2)[CH2:12][CH:13]1[CH2:33][CH2:14]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59251060HCID 59251060, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 24936969HCID 24936969, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-tert-butyl-3-(3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethylhex-5-enyl)urea (20 mg, 0.046 mmol) in anhydrous DCE (2 mL) at −10 C was added diethylzinc solution (0.46 mL, 0.46 mmol) and methyldiiodide (245 mg, 0.92 mmol) under nitrogen. Allowed reaction mixture to warm to RT and stirred overnight. The mixture was poured into sat NH4Cl, extracted with DCM (2×10 mL), dried (Na2SO4) and purified by HPLC to give 11 mg (50% yield) of 1-tert-butyl-3-(4-cyclopropyl-3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethylbutyl)urea. MS found: (M+H)+=451.

Workup

  1. additionThe mixture was poured
  2. extractionextracted with DCM (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-b9e5b00f9f8f46b98bd9f38775d32d4f
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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