Triethylamine → HCID 57761843, compound

HRID 230951Notes

Reaction equation

HRID 230951 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21]O)[CH:16]=[CH:17][CH:18]=3)[CH:10]=[C:9]([N:23]3[CH2:28][CH2:27][N:26]([C:29]4[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:25][CH2:24]3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:39]([N:41](CC)[CH2:42]C)C.CS(Cl)(=O)=O>C(Cl)Cl>[CH3:39][N:41]([CH3:42])[CH2:21][CH2:20][CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:11]2[CH:10]=[C:9]([N:23]3[CH2:24][CH2:25][N:26]([C:29]4[C:34]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:27][CH2:28]3)[N:8]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[N:12]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57761438HCID 57761438, compound

Product 1

HCID 57761843HCID 57761843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 3-(3-{2-morpholin-4-yl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-4-yl}-phenyl)-propan-1-ol (104 mg, 0.197 mmol) in methylene chloride and add triethylamine (55 μL, 0.394 mmol). Bring the solution to 0° C. with an ice bath and add methanesulfonyl chloride (23 μL, 0.394 mmol) dropwise. After 2 hours, dilute the reaction with additional methylene chloride and wash the mixture with brine (1×) in a separatory funnel. Dry the organic layer (Na2SO4) and concentrate under reduced pressure to give the title compound, which was used without further purification.

Workup

  1. additiondilute
  2. washwash the mixture with brine (1×) in a separatory funnel
  3. dry with materialDry the organic layer (Na2SO4)
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-19654126fe0c4f849cd174ed9ab12858
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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