Ammonium Chloride → HCID 66738525, compound

HRID 2047075Notes

Reaction equation

HRID 2047075 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C(C)([O-])C.[K+].[CH3:13][Si:14]([CH3:50])([CH3:49])[CH2:15][CH2:16][O:17][CH2:18][N:19]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:20]1[N:25]2[N:26]=[CH:27][CH:28]=[C:24]2[N:23]=[C:22]([CH:29]2[CH2:34][CH2:33][C:32](=[CH:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:31][CH2:30]2)[CH:21]=1.[NH4+].[Cl-]>CS(C)=O.[Na+].[Cl-]>[CH3:46][Si:45]([CH3:48])([CH3:47])[CH2:44][CH2:43][O:42][CH2:41][N:19]([CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:13])([CH3:49])[CH3:50])[C:20]1[N:25]2[N:26]=[CH:27][CH:28]=[C:24]2[N:23]=[C:22]([CH:29]2[CH2:34][CH2:33][C:32]3([CH:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:7]3)[CH2:31][CH2:30]2)[CH:21]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 66733552Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate

Product 1

HCID 66738525HCID 66738525, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 5234Sodium ChlorideSolvent

Procedure

To 50 mL roundbottom flask containing trimethylsulfoxonium iodide (3.57 mmol, 785 mg) in DMSO (8 mL) was added potassium tert-butoxide (3.57 mmol, 401 mg). This suspension was allowed to stir at room temperature for 3 hours. After 3 hours, ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate (1.78 mmol, 1.00 g) was added in 2 mL DMSO. The resulting solution was stirred at room temperature for 18 hours. After 18 hours, the reaction was diluted with saturated NaCl(aq) (30 mL). The pH was adjusted to ˜7 with saturated NH4Cl(aq) and extracted with DCM (50 mL) 4 times. The combined organics are dried over Na2SO4 and reduced in vacuo. The resulting residue was purified via flash chromatography to yield the title compound.

Workup

  1. waitAfter 3 hours
  2. stirringThe resulting solution was stirred at room temperature for 18 hours
  3. waitAfter 18 hours
  4. extractionextracted with DCM (50 mL) 4 times
  5. dry with materialThe combined organics are dried over Na2SO4
  6. customThe resulting residue was purified via flash chromatography

Sources & evidence

ORD record
ord-db3e55cb25ef4a0098d1604ed293ab75
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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