Ammonia → HCID 59088575, compound

HRID 1070452Notes

Reaction equation

HRID 1070452 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:30][C:31]([OH:33])=O)[CH2:10][N:11]([CH3:29])[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][CH3:25])=[C:16]([Br:26])[C:15]=2[O:27][CH3:28])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].C1C=CC2N(O)N=[N:40]C=2C=1.N.Cl.C(N=C=NCCCN(C)C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:30][C:31](=[O:33])[NH2:40])[CH2:10][N:11]([CH3:29])[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][CH3:25])=[C:16]([Br:26])[C:15]=2[O:27][CH3:28])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22397024HCID 22397024, compound

Product 1

HCID 59088575HCID 59088575, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-[2-(3,4-dichlorophenyl)-3-carboxypropyl]—N-methyl-3-bromo-2,4-dimethoxy-1-napthamide (0.26 g, 0.468 mmol) in 5 mL of DMF was added HOBT.NH3 (0.175 g, 1.15 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.184 g, 0.96 mmol). The mixture was stirred at RT for 24 h and treated with saturated NaHCO3. The aqueous layer was extracted with DCM. The combined DCM extracts was dried over MgSO4, filtered and concentrated. Following chromatography purification, the title compound was obtained as light yellow solid (0.21 g, 81% yield). 1H NMR (CDCl3) δ 8.15-8.02 (m), 7.61-7.43 (m), 7.37-7.26 (m), 7.07-7.00 (m), 6.91-6.89 (d), 6.81 (d), 6.70-6.67 (d), 6.56-6.53 (d), 6.14 (s), 5.88 (s), 5.33-5.30 (m), 4.33-4.26 (m), 4.05-3.64 (m), 3.43 (m), 3.25 (s), 3.20 (s), 2.96 (s), 2.89 (s), 2.82-2.55 (m), 1.59 (s). MS m/z 555.0 (M+). Analysis calculated for C24H23BrCl2N2O4, 0.1 H2O, C 51.84, H 4.21, N, 5.04, found C, 51.81, H, 4.31, N, 5.05.

Workup

  1. extractionThe aqueous layer was extracted with DCM
  2. dry with materialThe combined DCM extracts was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatography purification

Sources & evidence

ORD record
ord-4ed64d471b764bd897c35001ec4add32
Source dataset
uspto-grants-2005_06
Patent number
US06903092B2

Reaction notes

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