Water → HCID 58706591, compound

HRID 1716515Notes

Reaction equation

HRID 1716515 reaction equation
[NH2:1][C@H:2]([C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][N:18]=3)[N:11]=2)=[CH:8][N:9]=1)[CH2:3][OH:4].C(N(CC)CC)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl.O>C(Cl)(Cl)Cl>[CH3:23][C:21]1[CH:20]=[CH:19][N:18]=[C:17]([NH:16][C:12]2[N:11]=[C:10]([C:7]3[S:6][C:5]([C@@H:2]4[CH2:3][O:4][C:32](=[O:34])[NH:1]4)=[N:9][CH:8]=3)[CH:15]=[CH:14][CH:13]=2)[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 58706673HCID 58706673, compound

Product 1

HCID 58706591HCID 58706591, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (S)-2-amino-2-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}ethanol (220 mg, 0.67 mmol) obtained in Example 13, triethylamine (0.93 ml, 0.67 mmol) in chloroform (5 ml), triphosgene (70 mg, 0.24 mmol) was added while cooled to −78° C., and the mixture was stirred at the same temperature for 3 hours. The reaction solution was warmed to room temperature and water was added and it was extracted with ethyl acetate. After washed with a saturated saline solution, the organic layer was dried over magnesium sulfate. After concentrated, the residue was washed with ethanol and the title compound (41 mg, 17%) was obtained.

Workup

  1. temperatureThe reaction solution was warmed to room temperature
  2. extractionit was extracted with ethyl acetate
  3. washAfter washed with a saturated saline solution
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationAfter concentrated
  6. washthe residue was washed with ethanol

Sources & evidence

ORD record
ord-c541a63431924bab946d8c5b14006f54
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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