Triethylamine → 2-({3-Nitro-4-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]phenyl}carbonyl)benzoic acid

HRID 2414306Notes

Reaction equation

HRID 2414306 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][O:10][C:9]2=[O:18])[CH2:4][CH2:3]1.Cl[C:20]1[CH:36]=[CH:35][C:23]([C:24]([C:26]2[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=2[C:28]([OH:30])=[O:29])=[O:25])=[CH:22][C:21]=1[N+:37]([O-:39])=[O:38].C(N(CC)CC)C>CN(C)C=O>[N+:37]([C:21]1[CH:22]=[C:23]([C:24]([C:26]2[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=2[C:28]([OH:30])=[O:29])=[O:25])[CH:35]=[CH:36][C:20]=1[N:2]1[CH2:3][CH2:4][CH:5]([N:8]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][O:10][C:9]2=[O:18])[CH2:6][CH2:7]1)([O-:39])=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 665622-(4-Chloro-3-nitrobenzoyl)benzoic acidHCID 220630891-(4-Piperidinyl)-1,2-dihydro-4H-3,1-benzoxazin-2-one hydrochloride

Product 1

HCID 99357602-({3-Nitro-4-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]phenyl}carbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-piperidin-4-yl-1,4-dihydro-2H-3,1-benzoxazin-2-one hydrochloride (J.Med. Chem. 1998, 2157) (0.8 g), 2-(4-chloro-3-nitrobenzoyl)benzoic acid (0.9 g) and triethylamine (0.8 ml) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 72 h. The mixture was partitioned between ethyl acetate and dilute hydrochloric acid, the organic layer was evaporated under reduced pressure. Purification was by chromatography eluting with 4% methanol/dichloromethane. The residue was triturated from methanol, yield 0.4 g as a solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate and dilute hydrochloric acid
  2. customthe organic layer was evaporated under reduced pressure
  3. customPurification
  4. washeluting with 4% methanol/dichloromethane
  5. customThe residue was triturated from methanol, yield 0.4 g as a solid

Sources & evidence

ORD record
ord-4ea4988319d24178a20b54e0e7a08f19
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

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