(Diethylamino)sulfur trifluoride → HCID 178526820, compound

HRID 1819442Notes

Reaction equation

HRID 1819442 reaction equation
[N+:1]([C:4]1[C:5]([NH:23][CH2:24][C@H:25]2[CH2:30][CH2:29][C@H:28]([N:31]3[CH2:34][CH:33](O)[CH2:32]3)[CH2:27][CH2:26]2)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:22])([F:21])[F:20])=[N:8][CH:9]=1)([O-:3])=[O:2].C(N(S(F)(F)[F:42])CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:42][CH:33]1[CH2:34][N:31]([C@H:28]2[CH2:27][CH2:26][C@H:25]([CH2:24][NH:23][C:5]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]([NH:10][CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[O:18][C:19]([F:20])([F:21])[F:22])[N:6]=3)[CH2:30][CH2:29]2)[CH2:32]1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 178526822HCID 178526822, compound

Product 1

HCID 178526820HCID 178526820, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)azetidin-3-ol (100 mg, 0.20 mmol) in CH2Cl2 (25 mL) was added dropwise a solution of diethylaminosulfur trifluoride (32 μL, 0.24 mmol) in CH2Cl2 (0.5 mL) at room temperature over a period of 15 min. When the reaction was complete, the mixture was treated with saturated NaHCO3 and stirred for 5 min. The organic phase was separated and washed with water. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as eluent to afford 26 mg of the title compound as a pale yellow solid (26%), m/z 499.1 [M+1]+.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-6a7fbc66f28743c78214ca80ac89e0fe
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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