Morpholine → HCID 89876426, compound

HRID 1487085Notes

Reaction equation

HRID 1487085 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([S:14](=[O:29])(=[O:28])[N:15]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][CH:21]=2)[CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].BrC(Br)=O.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>O1CCCC1>[CH2:26]([C:23]1[CH:22]=[CH:21][C:20]([N:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[S:14]([C:11]2[CH:12]=[CH:13][C:4]([C:1](=[O:3])[CH2:2][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:5]([CH:10]=2)[C:6]([O:8][CH3:9])=[O:7])(=[O:28])=[O:29])=[CH:25][CH:24]=1)[CH3:27]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 79057Carbonyl bromideHCID 89876280HCID 89876280, compound

Product 1

HCID 89876426HCID 89876426, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phenyltrimethylaminotribromide (100 mg, 0.266 mmol) in tetrahydrofuran (THF) (0.5 mL) was added dropwise over 5 minutes, to a solution of methyl 2-acetyl-5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)benzoate (105 mg, 0.251 mmol) in THF (1.5 mL) at room temperature, under nitrogen. The orange solution was stirred for 1 hour to give a yellow solution containing a white precipitate. Analysis showed major product to be the desired intermediate bromoketone. The precipitate was filtered off and the solution was treated with morpholine (0.066 mL, 0.754 mmol). The resulting suspension was stirred for 30 minutes and partitioned between ammonium chloride solution (10 mL) and ethyl acetate (2×5 mL). The dried (MgSO4) extract was evaporated to give the desired product (65 mg), as an orange gum, which was used directly in the next step. LCMS [LCMS1] Rt 1.06 min, m/z (ES+) 503 (M+H).

Workup

  1. customto give a yellow solution
  2. additioncontaining a white precipitate
  3. filtrationThe precipitate was filtered off
  4. stirringThe resulting suspension was stirred for 30 minutes
  5. custompartitioned between ammonium chloride solution (10 mL) and ethyl acetate (2×5 mL)
  6. dry with materialThe dried (MgSO4)
  7. extractionextract
  8. customwas evaporated

Sources & evidence

ORD record
ord-10499de5a75343049aff660d66736828
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

Loading…