Water → HCID 66616612, compound

HRID 1889634Notes

Reaction equation

HRID 1889634 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:10]([C:18]([OH:20])=O)[CH:9]=2)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.[F:44][C:45]1[CH:50]=[CH:49][C:48]([CH2:51][NH2:52])=[CH:47][CH:46]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([C:18](=[O:20])[NH:52][CH2:51][C:48]3[CH:49]=[CH:50][C:45]([F:44])=[CH:46][CH:47]=3)[CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=2)=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 962WaterHCID 673264-FluorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66616568HCID 66616568, compound

Product 1

HCID 66616612HCID 66616612, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 4′-fluoro-5-(methoxycarbonyl)biphenyl-3-carboxylic acid (400 mg, 1.459 mmol) in DMF/CH2Cl2 at rt was added EDCI.HCl (363 mg, 1.896 mmol) followed by HOBt.H2O (197 mg, 1.459 mmol). After one minute, (4-fluorophenyl)methanamine (183 mg, 1.459 mmol) was added to the mixture and the reaction mixture was stirred at rt for 4 h. To the reaction mixture were added EtOAc and aq. NaHCO3. The EtOAc layer was separated, washed with water, dried over MgSO4 and concentrated in vacuo to obtain a crude product as a light yellow solid (585 mg, >100% yield), MS: M+H=382.21. The crude product was used directly in the next step without further purification. 1H NMR (CDCl3): δ 8.39 (s, 1H), 8.32 (s, 1H), 7.58˜7.02 (m, 9H), 4.63 (d, J=6.0 Hz, 2H), 3.95 (s, 3H).

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-467034407867456dbe04df494c32b000
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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