2-Morpholinoethylamine → HCID 15940239, compound

HRID 1671781Notes

Reaction equation

HRID 1671781 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[O:15][CH:14]=[N:13][C:12]=3[C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C1COCC1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:12]2[N:13]=[CH:14][O:15][C:11]=2[C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[S:3][C:4]=3[CH:10]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 57527166HCID 57527166, compound

Product 1

HCID 15940239HCID 15940239, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-6-(4-(4-fluorophenyl)oxazol-5-yl)benzo[d]thiazole (0.030 g, 0.080 mmol, 1.0 eq.) and 4-(2-aminoethyl)morpholine (0.073 mL, 0.556 mmol, 7.0 eq.) in THF (1.5 mL) was mechanically shaken at 54° C. overnight. After cooling to room temperature, the solution was concentrated in vacuo. MeOH was added to the residue, and the mixture was subjected to autoprep. The appropriate fractions were collected, and NaHCO3 (s) was added. The solution was then concentrated in vacuo not to dryness and extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to give 6-(4-(4-fluorophenyl)oxazol-5-yl)-N-(2-morpholinoethyl)benzo[d]thiazol-2-amine as a light yellow solid (0.0182 g, 54% yield). LC/MS (MH)=425.17.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionMeOH was added to the residue
  3. customThe appropriate fractions were collected
  4. additionNaHCO3 (s) was added
  5. concentrationThe solution was then concentrated in vacuo not to dryness
  6. extractionextracted with CH2Cl2 (3×)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28a5cd0a3b6f4ae381a618265dd49298
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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