Triethylamine → HCID 59828906, compound

HRID 1191053Notes

Reaction equation

HRID 1191053 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].[CH3:14][C:15]([CH3:19])([CH3:18])[CH2:16][NH2:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:14][C:15]([CH3:19])([CH3:18])[CH2:16][NH:17][C:11]([CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)=[O:13]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 79882NeopentylamineHCID 93617423-(4-Cyanophenyl)-propionic acid

Product 1

HCID 59828906HCID 59828906, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine 3-(4-cyanophenyl)-propionic acid (870 mg, 4.9 mmol), 2,2-dimethylpropylamine (0.6 mL, 5.4 mmol), EDCI (1.0 g, 5.4 mmol), HOBT (804 mg, 5.9 mmol), triethylamine (2 mL, 14.8 mmol) and DMAP (60.5 mg, 0.5 mmol) in anhydrous DCM (50 mL). Stir at room temperature for 1 day under nitrogen. Concentrate the mixture in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:1) to obtain the desired intermediate as a white solid (740 mg, 61%). MS (ES+) m/z: 245 (M+H)+.

Workup

  1. concentrationConcentrate the mixture in vacuo
  2. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-a8d0188d5ef3475c814da79eeaba737d
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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