Triethylamine → HCID 131724455, compound

HRID 352246

Reaction equation

HRID 352246 reaction equation
N[CH:2]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([Cl:17])[C:11]=3[C:10]3=[N:18][O:19][C:20]([CH3:21])=[C:9]3[C:8]2=[O:22])[CH2:3]1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:35][C:36]([OH:38])=O)[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32].CC[N:41](CC)CC.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:17][C:12]1[C:11]2[C:10]3[C:9](=[C:20]([CH3:21])[O:19][N:18]=3)[C:8](=[O:22])[N:7]([C:4]3([C:29]4([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=[C:27]([CH2:35][C:36]([NH2:41])=[O:38])[CH2:28]4)[CH2:3][CH2:2][CH2:6][CH2:5]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 703723,4,5-Trimethoxyphenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 22713955HCID 22713955, compound

Product 1

HCID 131724455HCID 131724455, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of racemic 5-(3-aminocyclopentyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (81 mg, 0.26 mmol) in CH2Cl2 (3 mL) was added 3,4,5-trimethoxy phenyl acetic acid (114 mg, 0.52 mmol), Et3N (0.1 mL, 0.50 mmol), HOBt (41 mg, 0.3 mmol),DMAP (catalytic amount) and EDCI (72 mg, 0.38 mmol). The reaction mixture was stirred at r.t. for 18 hours. The mixture was diluted with CH2Cl2, washed (brine), dried (Na2SO4), filtered and concentrated. Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave the racemic title compound (89 mg, 66%). Mass Spectrum (FIA) (m/z) 454.0 (M+1)

Workup

  1. washwashed (brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f64bbca03c94c9d838d6d8d06135089
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

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