Triethylamine → HCID 20726108, compound

HRID 1582489Notes

Reaction equation

HRID 1582489 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=3[O:33][CH3:34])[CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:42](Cl)(=[O:46])[CH:43]([CH3:45])[CH3:44]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]([C:42](=[O:46])[CH:43]([CH3:45])[CH3:44])[C:10]([C:20]3[CH:21]=[C:22]([CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:30]=[CH:31][C:32]=3[O:33][CH3:34])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 10217738HCID 10217738, compound

Product 1

HCID 20726108HCID 20726108, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{3-[4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-4-methoxy-benzyl}-morpholine (100 mg, 0.20 mmol, as in the U.S. Provisional applications incorporated by reference herein, Example 31) in methylene chloride (10 mL) were sequentially added triethylamine (0.10 mL, 0.712 mmol) and isobutyryl chloride (42 μL, 0.392 mmol). The reaction mixture was stirred for 12 h. The solvents were removed under reduced pressure. Saturated sodium bicarbonate (2 mL) and methylene chloride (20 mL) were added and the layers were separated. The aqueous layer was extracted with methylene chloride (1×100 mL). The combined organic extracts were evaporated. Purification of the crude residue by Biotage flash chromatography eluting with 0-5% methanol in ethyl acetate gave 1-[4,5-bis-(4-chloro-phenyl)-2-(2-methoxy-5-morpholin-4-ylmethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-2-methyl-propan-1-one. HR-MS (ES, m/z) calculated for C31H34N3O3Cl2[(M+H)+]566.1972, observed 566.1977.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionSaturated sodium bicarbonate (2 mL) and methylene chloride (20 mL) were added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with methylene chloride (1×100 mL)
  5. customThe combined organic extracts were evaporated
  6. customPurification of the crude residue by Biotage flash chromatography
  7. washeluting with 0-5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-013c32e8e37f412f995753ef445c0ded
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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