Triethylamine → HCID 67539565, compound

HRID 1192379Notes

Reaction equation

HRID 1192379 reaction equation
C(N(CC)CC)C.[C:8]([NH:15][C@@H:16]([C:25]([OH:27])=O)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl.Cl.[N:30]1([C:36]2[N:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]3=[N:38][CH:37]=2)[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH-].[Na+]>CN(C=O)C.O>[C:11]([O:10][C:8](=[O:9])[NH:15][C@H:16]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:25]([N:33]1[CH2:34][CH2:35][N:30]([C:36]2[N:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]3=[N:38][CH:37]=2)[CH2:31][CH2:32]1)=[O:27])([CH3:12])([CH3:13])[CH3:14]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 67539435853680-34-9

Product 1

HCID 67539565HCID 67539565, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.30 mL, 2.18 mmol) was added to a solution of (R)—N-Boc-4-chlorophenylalanine (392 mg, 1.31 mmol), 3-piperazin-1-yl-imidazo[1,2-a]pyridine dihydrochloride (300 mg, 1.09 mmol), and 1-hydroxybenzotriazole (177 mg, 1.31 mmol) in DMF (5 mL) followed by the addition of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (251 mg, 1.31 mmol) in a single portion. After being stirred for 12 hours, the mixture was diluted with H2O, basified to pH 12 with 1.0 M NaOH, and extracted with DCM. The DCM extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was chromatographed (SiO2) using DCM:Et2O (1:1) followed by 10% MeOH/DCM as eluent to give (R)-[1-(4-chlorobenzyl)-2-(4-imidazo[1,2-a]pyridin-3-yl-piperazin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (350 mg).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe DCM extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (SiO2)

Sources & evidence

ORD record
ord-026e8f60d1ea4608b75be9c155ede11e
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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