Morpholine → HCID 136197323, compound

HRID 539873Notes

Reaction equation

HRID 539873 reaction equation
[Br:1][C:2]1[C:3](=[O:25])[NH:4][C:5]([C:11]2[CH:16]=[C:15]([C:17](=[O:20])[CH2:18]Br)[CH:14]=[CH:13][C:12]=2[O:21][CH2:22][CH2:23][CH3:24])=[N:6][C:7]=1[CH:8]([CH3:10])[CH3:9].C(N(CC)CC)C.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>ClCCl>[Br:1][C:2]1[C:3](=[O:25])[NH:4][C:5]([C:11]2[CH:16]=[C:15]([C:17](=[O:20])[CH2:18][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH:14]=[CH:13][C:12]=2[O:21][CH2:22][CH2:23][CH3:24])=[N:6][C:7]=1[CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 136197298HCID 136197298, compound

Product 1

HCID 136197323HCID 136197323, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (150 mg, 0.32 mmol) of example 71 was dissolved in dichloromethane (20 ml), added with triethylamine (0.5 ml) and morpholine (40 mg, 0.46 mmol), followed by stirring for 12 h. The reaction mixture was washed orderly with water (10 ml) and saturated saline. The organic phase was dried with anhydrous Na2SO4, and concentrated under reduced pressure to give an oil, which was passed through a silica gel column to obtain the title compound (60 mg, yield: 39%). 1H NMR (CDCl3) δ: 11.20 (1H, br), 9.21 (1H, d), 8.17 (1H, dd), 7.15 (1H, d), 4.30 (2H, t), 3.75-3.64 (10H, br), 3.52 (1H, m), 2.03 (2H, m), 1.30 (6H, d), 1.16 (3H, t).

Workup

  1. washThe reaction mixture was washed orderly with water (10 ml) and saturated saline
  2. dry with materialThe organic phase was dried with anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil, which

Sources & evidence

ORD record
ord-30912362de2f471fa61dfe6b7530312b
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

Loading…