HCID 24739395, compound → HCID 25115991, compound

HRID 424630Notes

Reaction equation

HRID 424630 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH3:21])[CH2:14][CH2:15][O:16][CH2:17][C:18]([OH:20])=O)(=[O:12])=[O:11])=[C:5]([CH3:22])[C:4]=1[CH3:23].[CH3:24][N:25]([CH:27]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)[CH3:26]>C1COCC1>[CH3:26][N:25]([CH:27]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH:28]1[CH2:29][CH2:30][CH:31]([NH:34][C:18](=[O:20])[CH2:17][O:16][CH2:15][CH2:14][N:13]([S:10]([C:6]2[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:23])[C:5]=2[CH3:22])(=[O:11])=[O:12])[CH3:21])[CH2:32][CH2:33]1)[CH3:24]

Participants

4

Reactant 2

HCID 24739395HCID 24739395, compound2×HCID 57786843HCID 57786843, compound2×

Product 1

HCID 25115991HCID 25115991, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N,N′-Carbonyldiimidazole (195 mg, 1.2 mmol) was added to a soln. of {2-[(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-methylamino]-ethoxy}-acetic acid (Intermediate C) (346 mg, 1 mmol) in THF (5 ml) and the mixture was stirred at RT for 1 h. A soln. of 4-(dimethylaminophenylmethyl)-cyclohexylamine (Intermediate VII) (256 mg, 1.1 mmol) in THF (5 ml) was then added and the reaction mixture was stirred at RT for 3 d. Thereafter, the soln. was concentrated i. vac., the residue was taken up in NaHCO3 soln. and the mixture was extracted with MC (3×30 ml). The combined organic phases were dried with Na2SO4 and concentrated i. vac. Further purification was carried out by means of flash chromatography with CHCl3/MeOH (95:5).

Workup

  1. concentrationwas concentrated i
  2. extractionand the mixture was extracted with MC (3×30 ml)
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. concentrationconcentrated i
  5. customFurther purification

Sources & evidence

ORD record
ord-9a4438fa32d943608ec7a4d30f395729
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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