Phenyl chloroformate → HCID 59380021, compound

HRID 2353754Notes

Reaction equation

HRID 2353754 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([C:14]([S:17]([C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)(=[O:19])=[O:18])([CH3:16])[CH3:15])[N:11]=[C:10]([C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=2)[N:9]=1.C(=O)(O)[O-].[Na+].Cl[C:39]([O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:40]>O1CCOCC1.C(OCC)C>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([C:14]([S:17]([C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)(=[O:19])=[O:18])([CH3:16])[CH3:15])[N:11]=[C:10]([C:26]2[CH:27]=[CH:28][C:29]([NH:30][C:39](=[O:40])[O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:31][CH:32]=2)[N:9]=1

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379932HCID 59379932, compound

Product 1

HCID 59380021HCID 59380021, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-[2-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]propan-2-yl]pyrimidin-2-yl]aniline (340 mg, 0.72 mmol) in 1,4-dioxane (4 mL) was added sodium bicarbonate (90 mg, 1.08 mmol). Phenyl chloroformate (0.104 mL, 0.83 mmol) was then added dropwise and the resulting mixture was stirred at RT for 6 hours. Reaction mixture was then evaporated and the residue was partitioned between DCM (5 mL) and water (5 mL). The organic layer was separated and aqueous re-extracted with more DCM (5 mL). The combined organic layers were combined and evaporated to dryness to afford an amber gum, which was taken up in diethyl ether (5 mL) and triturated with sonication. The resultant solid was collected by suction filtration and dried to afford the desired material (334 mg).

Workup

  1. customReaction mixture
  2. customwas then evaporated
  3. customthe residue was partitioned between DCM (5 mL) and water (5 mL)
  4. customThe organic layer was separated
  5. extractionaqueous re-extracted with more DCM (5 mL)
  6. customevaporated to dryness
  7. customto afford an amber gum, which
  8. customtriturated with sonication
  9. filtrationThe resultant solid was collected by suction filtration
  10. customdried

Sources & evidence

ORD record
ord-e67ce77ac75a479e90209a9e173bdd71
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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