Ammonium Chloride → HCID 25050519, compound

HRID 1020245Notes

Reaction equation

HRID 1020245 reaction equation
B([O-])=O.[Li+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:9][NH:10][C:11](=[O:24])[NH:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][C:19](OCC)=[O:20])[N:17]=1.[Cl-].[NH4+]>C1COCC1.O>[Cl:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:9][NH:10][C:11]([NH:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][CH2:19][OH:20])[N:17]=1)=[O:24]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 123308Lithium metaborateHCID 86622746HCID 86622746, compound

Product 1

HCID 25050519HCID 25050519, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Lithium boranate (7 mg, 322 μmol) was added to a solution of Ethyl 2-(2-(3-(3,4-dichlorobenzyl)ureido)thiazol-4-yl)acetate (Example 35) (58 mg, 150 μmol) in dry THF (4 ml) at 0° C. The reaction mixture was stirred for 3 hours at this temperature and then allowed to warm to ambient temperature overnight. Then, saturated aqueous ammonium chloride solution (3 ml) was added and the mixture was stirred for 2 hours. The salts were dissolved by addition of a few drops of water, and the mixture was extracted several times with ethyl acetate. The combined organic layers were partitioned with brine and then dried over sodium sulfate, filtered, and volatiles removed in vacuo. The crude material was purified by column chromatography (silica gel, acetone/ethyl acetate, 1:20, 1:15, 1:10), yielding the title compound in 60% (32 mg, 92 mmol). 1H NMR (300 MHz, CD3OD) δ 2.80 (t, 2H), 3.81 (t, 2H), 4.40 (s, 2H), 6.60 (s, 1H), 7.24 (dd, 1H), 7.42-7.48 (m, 2H). MS (ES+): M/Z 346 and 348 (M+H).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionthe mixture was extracted several times with ethyl acetate
  3. customThe combined organic layers were partitioned with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customvolatiles removed in vacuo
  7. customThe crude material was purified by column chromatography (silica gel, acetone/ethyl acetate, 1:20, 1:15, 1:10)

Sources & evidence

ORD record
ord-fb5ed5c8c31a42ae8b9e7a7fe88a50ab
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

Loading…