Methanesulfonyl chloride → HCID 57562598, compound

HRID 1725478Notes

Reaction equation

HRID 1725478 reaction equation
[CH3:1][Si:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[C:17]([CH2:19]O)[CH:16]=[N:15][CH:14]=2)=[N:8]1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[O:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[O:43][CH:44]1[CH2:50][NH:49][CH2:48][CH2:47][NH:46][CH2:45]1>C(Cl)(Cl)Cl>[O:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[O:43][CH:44]1[CH2:50][N:49]([CH2:19][C:17]2[N:18]=[C:13]([NH:12][C:9]3[CH:10]=[CH:11][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:22])([CH3:21])[CH3:1])[N:8]=3)[CH:14]=[N:15][CH:16]=2)[CH2:48][CH2:47][NH:46][CH2:45]1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57562597HCID 57562597, compoundHCID 57562606HCID 57562606, compound

Product 1

HCID 57562598HCID 57562598, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 44.9 mg of (6-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)pyrazin-2-yl)methanol, 73 μl of N,N-diisopropylethylamine and 4 ml of chloroform was added 16 g of methanesulfonyl chloride at room temperature followed by stirring for 1 hour. The reaction mixture was dropped into a solution of 6-(tetrahydro-2H-pyran-2-yloxy)-1,4-diazepane obtained in Reference Example 5 in 2 ml of chloroform, and the reaction mixture was stirred at room temperature for 15 hours. The resulting reaction mixture was washed with water and brine. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The resulting residue was purified by a basic thin-layer chromatography (eluent: chloroform/methanol=30/1) to give the title compound.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 15 hours
  2. customThe resulting reaction mixture
  3. washwas washed with water and brine
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by a basic thin-layer chromatography (eluent: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-c6fdd94edcc14539858cbf6531717070
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

Loading…