Hydrochloric Acid → HCID 22093480, compound

HRID 457989Notes

Reaction equation

HRID 457989 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8](=[O:23])[C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:12]([F:21])=[CH:11][C:10]=2[OH:22])=[C:4]([F:26])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].Cl>CC(C)=O>[CH2:38]([O:37][C:35](=[O:36])[CH2:34][O:22][C:10]1[CH:11]=[C:12]([F:21])[C:13]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[CH:14][C:9]=1[C:8](=[O:23])[NH:7][CH2:6][C:5]1[CH:24]=[CH:25][C:2]([Br:1])=[CH:3][C:4]=1[F:26])[CH3:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18468208HCID 18468208, compound

Product 1

HCID 22093480HCID 22093480, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N-(4-bromo-2-fluoro-benzyl)-4-fluoro-2-hydroxy-5-morpholin-4-yl-benzamide (0.8 g, 2.13 mmol) in acetone (11 mL), was treated with aq 2 N K2CO3 (1.6 mL, 3.20 mmol) and ethyl bromoacetate (0.35 mL, 3.20 mmol), and heated to 50° C. After stirring for 30 min, the reaction was cooled to room temperature and acidified to pH 7 with aq 2 N HCl. The resulting solution was extracted with ethyl acetate and washed with saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated to give [2-(4-bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-morpholin-4-yl-phenoxy]-acetic acid ethyl ester (0.8 g, 81%): 1H NMR (DMSO-d6 300 MHz) δ 9.05 (t, J=6 Hz, 1 H), 8.18 (d, J=2.1 Hz, 1 H), 8.09 (ddd, J, =8.4 Hz, J2=2.4 Hz, J3=0.9 Hz, 1 H), 7.79 (d, J=7.8 Hz, 1 H), 7.61 (t, J=8.0 Hz, 1 H), 7.54 (d, J=10.2 Hz, 1 H), 7.15 (d, J=14.1 Hz, 1 H), 4.94 (s, 2 H), 4.63 (d, J=6 Hz, 2 H), 4.14 (q, J=7.2 Hz, 2 H), 3.71 (t, J=4.7 Hz, 4 H), 2.92 (t, J=4.7 Hz, 4 H), 1.16 (t, J=7.2 Hz, 3 H).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionThe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated NaCl
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a39dc87f413d4d51b53e5330d6706421
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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