2-Morpholinoethylamine → HCID 15940239, compound

HRID 1452948Notes

Reaction equation

HRID 1452948 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-d6c83bd2077542ecb97d9112070ae6c7
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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