Triethylamine → HCID 21949225, compound

HRID 2215604Notes

Reaction equation

HRID 2215604 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[C:20]([I:21])=[CH:19][N:18]=[C:17]([NH2:22])[N:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4].C(N([CH2:28][CH3:29])CC)C.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32]>O1CCCC1>[I:21][C:20]1[C:15]([O:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[N:5]([C:3]([NH:2][CH3:1])=[O:4])[CH:6]=[CH:7]3)=[N:16][C:17]([N:22]([C:31]([O:33][C:29]2[CH:28]=[CH:36][CH:35]=[CH:34][CH:39]=2)=[O:32])[C:31](=[O:32])[O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 21949275HCID 21949275, compound

Product 1

HCID 21949225HCID 21949225, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N1-Methyl-5-(2-amino-5-iodo-4-pyrimidyl)oxy-1H-1-indolecarboxamide (205 mg, 0.500 mmol) was suspended in tetrahydrofuran (5.0 ml); triethylamine (0.209 ml, 1.50 mmol) was added thereto while stirring. The suspension was cooled with ice; phenyl chloroformate (0.188 ml, 1.50 mmol) was added thereto; and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate; and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, and was dried over anhydrous magnesium sulfate. After solvent distillation, the obtained crude product was crystallized from ethyl acetate-hexane; and the crystals were filtered off, and dried under aeration to yield the title compound as white crystals (207 mg, 0.319 mmol, 64%).

Workup

  1. temperatureThe suspension was cooled with ice
  2. stirringand the reaction mixture was stirred at room temperature for 3 hours
  3. customThe reaction mixture was partitioned between ethyl acetate
  4. washand the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationAfter solvent distillation
  7. customthe obtained crude product
  8. customwas crystallized from ethyl acetate-hexane
  9. filtrationand the crystals were filtered off
  10. customdried under aeration

Sources & evidence

ORD record
ord-fdcc30a86c7a4cd09e05d0d6705489cb
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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