Ethylamine → HCID 68106478, compound

HRID 2403625Notes

Reaction equation

HRID 2403625 reaction equation
C(OC([NH:8][CH2:9][C:10]([N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([OH:29])=O)=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11])=O)(C)(C)C.C1C=C[C:33]2N(O)N=[N:36][C:34]=2C=1.C(N)C.N=C=N.[N-]=C=O.C(=O)([O-])[O-]>CN(C=O)C>[CH2:34]([NH:36][C:27]([C:24]1[CH:23]=[CH:22][C:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][N:12]([C:10](=[O:11])[CH2:9][NH2:8])[CH3:13])[CH:16]=2)=[CH:26][CH:25]=1)=[O:29])[CH3:33]

Participants

8

Reactant 6

HCID 6341EthylamineHCID 19660Carbonate IonHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 160435CarbodiimideHCID 68107209HCID 68107209, compound

Product 1

HCID 68106478HCID 68106478, compoundYield 319.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3′-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)biphenyl-4-carboxylic acid (9 mg) in DMF (1 ml) was added HOBt (2 mg) and ethylamine (2 mg), and PS-Carbodiimide (manufactured by Biotage AB) (100 mg) was added thereto, followed by shaking overnight. Thereafter, PS-Isocyanate (manufactured by Biotage AB) and MP-Carbonate (manufactured by Biotage AB) were added in an amount of 50 mg, and DMF (0.5 ml) was further added thereto, followed by shaking for 2 hours. The insoluble material was filtered and the filtrate was concentrated. To the obtained residue was added MeOH (0.5 ml), and a 4 M hydrogen chloride/EtOAc solution (0.5 ml) was added thereto, followed by shaking for 1 hour. Thereafter, the reaction mixture was concentrated to obtain N-ethyl-3′-{[glycyl(methyl)amino]methyl}biphenyl-4-carboxamide (15.4 mg).

Workup

  1. additionwas added
  2. additionwas further added
  3. stirringby shaking for 2 hours
  4. filtrationThe insoluble material was filtered
  5. concentrationthe filtrate was concentrated
  6. additionTo the obtained residue was added MeOH (0.5 ml)
  7. additiona 4 M hydrogen chloride/EtOAc solution (0.5 ml) was added
  8. stirringby shaking for 1 hour
  9. concentrationThereafter, the reaction mixture was concentrated

Sources & evidence

ORD record
ord-fd2b19ae7fdf412fb0b0ec227bc53818
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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