HCID 68953639, compound → HCID 16041821, compound

HRID 1887468Notes

Reaction equation

HRID 1887468 reaction equation
Cl.[OH:2][C:3]1[C:4]([O:24][CH3:25])=[CH:5][C:6]2[CH2:15][CH2:14][N:13]3[CH:8]([CH2:9][C:10]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([OH:22])[C:11]=4[CH2:12]3)[C:7]=2[CH:23]=1>N1C=CC=CC=1>[C:3]([O:2][C:3]1[C:4]([O:24][CH3:25])=[CH:5][C:6]2[CH2:15][CH2:14][N:13]3[CH:8]([CH2:9][C:10]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][C:17](=[O:20])[CH3:16])[C:11]=4[CH2:12]3)[C:7]=2[CH:23]=1)(=[O:2])[CH3:23]

Participants

3

Reactant 1

HCID 68953639HCID 68953639, compound

Product 1

HCID 16041821HCID 16041821, compoundYield 129.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A product obtained in Example 2 (0.1 g, 0.27 ml) was dissolved in pyridine (10 ml), adding acetyl anhydride (0.5 ml). The mixture was stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure and added water. Then the aqueous phase was adjust to pH 8 with saturated NaHCO3 and extracted with CH2Cl2. The combined organic layers were washed with brine and dried over Na2SO4, filtered, and the solvent was evaporated under reduced pressure to give pale desired product (0.073 g, 64.6%). mp 212˜214° C. 1HNMR (CDCl3) δ: 2.33 (3H, s, COCH3), 2.34 (3H, s, COCH3), 2.63˜2.75 (3H, m, CH2), 3.13˜3.20 (3H, m, CH2), 3.41˜3.56 (2H, m, CH2 and N—CH), 3.81 (3H, s, Ar—OCH3), 3.82 (3H, s, Ar—OCH3), 4.02 (1H, d, CH2), 6.70 (1H, s, ArH), 6.83 (1H, d, ArH), 6.92 (1H, s, ArH), 7.00 (1H, s, ArH).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionadded water
  3. extractionextracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-893ae8836f5f4c1daafb5e7b586f18dd
Source dataset
uspto-grants-2013_08
Patent number
US08501762B2

Reaction notes

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