Water → HCID 66616501, compound

HRID 1889646Notes

Reaction equation

HRID 1889646 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:15]=2)[C:10]([OH:12])=O)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.[F:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][NH2:53])=[CH:48][CH:47]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl.CCOC(C)=O>[F:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][NH:53][C:10]([C:9]2[CH:13]=[C:14]([CH:15]=[C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:21][CH:20]=3)[CH:8]=2)[C:16]([O:18][CH3:19])=[O:17])=[O:12])=[CH:48][CH:47]=1

Participants

9

Reactant 6

HCID 962WaterHCID 673264-FluorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66616348HCID 66616348, compound

Product 1

HCID 66616501HCID 66616501, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 3-(4-fluorophenoxy)-5-(methoxycarbonyl)benzoic acid (2.2 g, 7.58 mmol) in DMF/CH2Cl2 at rt was added EDCI.HCl (1.889 g, 9.85 mmol) followed by HOBt.H2O (1.024 g, 7.58 mmol) with stirring. After one minute (4-fluorophenyl)methanamine (0.949 g, 7.58 mmol) was added to the mixture and it was stirred at rt for 4 h. EtOAc and aq NaHCO3 were added to the mixture. The EtOAc layer was separated, washed with water, dried over MgSO4 and concentrated in vacuo to obtain a crude product (2.7 g, 6.79 mmol, 90% yield) as a light yellow solid. The crude product was used in the next step without further purification. MS (ESI): (M+H)+=382.21.

Workup

  1. customThe EtOAc layer was separated
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1fe1915c113447ab046af2496f4bb82
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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