Phenylacetic Acid → Diisopropylethylamine

HRID 1631991Notes

Reaction equation

HRID 1631991 reaction equation
C(N1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:17]N(C(OC(C)(C)C)=O)[CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.F[C:26](F)(F)C(O)=O.CCN=C=NCCCN(C)C.Cl.C1(CC(O)=O)C=CC=CC=1.C1C=CC2N(O)N=NC=2C=1>ClCCl>[CH2:12]([N:11]([CH:10]([CH3:9])[CH3:26])[CH:14]([CH3:17])[CH3:15])[CH3:13]

Participants

7

Reactant 5

HCID 999Phenylacetic AcidHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23153143HCID 23153143, compound

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

450 mg (1.36 mmol) of tert-butyl 3-(4-benzylpiperazin-1-yl)azetidine-1-carboxylate (XXIe) were dissolved in dichloromethane (8 ml) and, while stirring at room temperature, trifluoroacetic acid (8 ml) was added. The reaction solution was stirred for 2 h and then the solvent and excess trifluoroacetic acid were removed in vacuo. The residue was taken up again in toluene, concentrated in vacuo and then dried in vacuo. 286 mg (1.49 mmol) of EDCl were added to a solution of 642 mg (1.36 mmol) of 6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydrobenzimidazol-1-yl]phenylacetic acid (XIIIa), 276 mg (2.03 mmol) of HOBt, the residue obtained above, and 2.13 ml (12.2 mmol) of ethyldiisopropylamine in 50 ml of dichloromethane while cooling in ice.

Workup

  1. stirringThe reaction solution was stirred for 2 h
  2. customthe solvent and excess trifluoroacetic acid were removed in vacuo
  3. concentrationconcentrated in vacuo
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9ed6757f7b18429db2b11c439695b106
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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