Sodium Carbonate → HCID 59380011, compound

HRID 2353721Notes

Reaction equation

HRID 2353721 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH3:11][C@H:12]1[CH2:17][O:16][CH2:15][CH2:14][N:13]1[C:18]1[CH:23]=[C:22]([C:24]([S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])([CH3:26])[CH3:25])[N:21]=[C:20]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[N:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:11][C@H:12]1[CH2:17][O:16][CH2:15][CH2:14][N:13]1[C:18]1[CH:23]=[C:22]([C:24]([S:27]([CH:30]([CH3:31])[CH3:32])(=[O:29])=[O:28])([CH3:26])[CH3:25])[N:21]=[C:20]([C:33]2[CH:39]=[CH:38][C:36]([NH:37][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:35][CH:34]=2)[N:19]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 15891Phenyl chloroformateHCID 59380063HCID 59380063, compound

Product 1

HCID 59380011HCID 59380011, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.42 mL, 3.34 mmol) was added dropwise to 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]aniline (1.4 g, 3.34 mmol) and sodium carbonate (0.421 g, 5.02 mmol) in dioxane (20 mL) under nitrogen. The resulting suspension was stirred at RT for 2 hours. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL) and washed with water (50 mL). The organic layer was dried (MgSO4), filtered and evaporated to give crude product which was triturated with diethyl ether to give the desired product (1.57 g).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in DCM (50 mL)
  3. washwashed with water (50 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product which
  8. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-a07da199d8514db1b3dcf9016aeb08b4
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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