Morpholine → 4-{4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-benzyl}-morpholine

HRID 623666

Reaction equation

HRID 623666 reaction equation
CS(Cl)(=O)=O.[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:16][C:15]=1[N:31]1[C:35]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42]O)=[CH:38][CH:37]=2)=[CH:34][N:33]=[N:32]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>C(Cl)Cl.CN(C=O)C>[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:16][C:15]=1[N:31]1[C:35]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:38][CH:37]=2)=[CH:34][N:33]=[N:32]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 67985193{4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-phenyl}-methanol

Product 1

HCID 679854174-{4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-benzyl}-morpholineYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TEA (160 μl, 1.17 mmol) and MsCl (90 μl, 1.17 mmol) were added to a solution of {4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-phenyl}-methanol (200 mg, 0.39 mmol) in DCM (5 ml) at 0° C. The solution was stirred for 30 minutes at 0° C. and for 12 hours at RT. The solvent was removed under reduced pressure and the reaction crude was dissolved in DMF (3 ml). Morpholine (1.17 mmol) and TEA (160 μl, 1.17 mmol) were added and the reaction mixture was stirred for 12 hours at RT. After standard work-up with AcOEt (4×30 ml) and washing with H2O (2×30 mL) and brine (2×30 ml), the solvent was evaporated under reduced pressure and the crude reaction mixture was purified by column chromatography (PE/AcOEt:20/80) to obtain the desired adduct as an oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe reaction crude
  3. stirringthe reaction mixture was stirred for 12 hours at RT
  4. washAfter standard work-up with AcOEt (4×30 ml) and washing with H2O (2×30 mL) and brine (2×30 ml)
  5. customthe solvent was evaporated under reduced pressure
  6. customthe crude reaction mixture
  7. customwas purified by column chromatography (PE/AcOEt:20/80)

Sources & evidence

ORD record
ord-c8c63ff405f8485cbd1e1dae2b349f79
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Linked notes

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