Azetidine → HCID 67055781, compound

HRID 602292Notes

Reaction equation

HRID 602292 reaction equation
[NH2:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]([C:6]([NH:8][CH2:9][C@@H:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23](C4NC=CN=4)=[O:24])[CH2:19][CH2:18]3)[CH2:11]2)=[O:7])=[C:4]([O:33][CH2:34][CH3:35])[CH:3]=1.[NH:36]1[CH2:39][CH2:38][CH2:37]1>C1COCC1>[NH2:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]([C:6]([NH:8][CH2:9][C@@H:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([N:36]4[CH2:39][CH2:38][CH2:37]4)=[O:24])[CH2:19][CH2:18]3)[CH2:11]2)=[O:7])=[C:4]([O:33][CH2:34][CH3:35])[CH:3]=1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 67055666HCID 67055666, compound

Product 1

HCID 67055781HCID 67055781, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-4-amino-5-chloro-2-ethoxy-N-[{4-[(1-imidazolecarbonyl-4-piperidinyl)-methyl]-2-morpholinyl}methyl]benzamide (Example 206) (1.07 g) and azetidine (0.25 g) in THF (15 ml) was heated to reflux for 19 hours with stirring. After cooling to room temperature, the reaction solution was dried under reduced pressure to be solidified, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (0.43 g) as a white solid. Melting point 166-168° C. (recrystallized from EA/H)

Workup

  1. temperatureto reflux for 19 hours
  2. customthe reaction solution was dried under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-e65585e18ab94a8db0b210f932dea3cc
Source dataset
uspto-grants-2011_03
Patent number
US07906510B2

Reaction notes

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