Ammonia → 4-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzamide

HRID 515483Notes

Reaction equation

HRID 515483 reaction equation
[C:1]1([C@H:7]([N:9]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=3)[O:12][CH2:11][CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.N.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)[N:32]=1>CN(C)C=O.O>[C:1]1([C@H:7]([N:9]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([NH2:32])=[O:21])=[CH:18][CH:17]=3)[O:12][CH2:11][CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 672831054-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzoic acid

Product 1

HCID 672820504-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzoic acid (diastereomer type A) (0.96 g, 2.9 mmol) and 7 mol/L methanol solution of ammonia (2 mL, 14 mmol) in N,N-dimethylformamide (10 mL) was added 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (1.25 g, 4.5 mmol) at room temperature and the mixture was stirred for one day. The reaction mixture was poured into water. The resulting white solid material was collected by filtration and dried under reduced pressure at 50° C. for 5 hours to yield 4-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzamide (diastereomer type A) (0.58 g, 1.78 mmol, 61%).

Workup

  1. filtrationThe resulting white solid material was collected by filtration
  2. customdried under reduced pressure at 50° C. for 5 hours

Sources & evidence

ORD record
ord-a77b7ebc592a4110b3d193610203c98a
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

Loading…