N,N-Dimethylglycine → 3-Chloro-N-[(1S)-2-[(N,N-dimethylglycyl)amino]-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]-4-[(1-methylethyl)oxy]benzamide

HRID 1697799Notes

Reaction equation

HRID 1697799 reaction equation
[NH2:1][CH2:2][C@@H:3]([NH:23][C:24](=[O:36])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH:32]([CH3:34])[CH3:33])=[C:27]([Cl:35])[CH:26]=1)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[C:18]([CH:19]([OH:21])[CH3:20])=[CH:17][CH:16]=[CH:15][N:14]3[CH:22]=2)=[CH:7][CH:6]=1.CCN=C=NCCCN(C)C.C(N(CC)C(C)C)(C)C.[CH3:57][N:58]([CH3:63])[CH2:59][C:60](O)=[O:61]>C(Cl)Cl.O>[Cl:35][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[O:31][CH:32]([CH3:33])[CH3:34])[C:24]([NH:23][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[C:18]([CH:19]([OH:21])[CH3:20])=[CH:17][CH:16]=[CH:15][N:14]3[CH:22]=2)=[CH:7][CH:6]=1)[CH2:2][NH:1][C:60](=[O:61])[CH2:59][N:58]([CH3:63])[CH3:57])=[O:36]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 57594408N-[(1S)-2-Amino-1-((4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]-3-chloro-4-[(1-methylethyl)oxy]benzamide

Product 1

HCID 116140733-Chloro-N-[(1S)-2-[(N,N-dimethylglycyl)amino]-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]-4-[(1-methylethyl)oxy]benzamideYield 48.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[(1S)-2-amino-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]-3-chloro-4-[(1-methylethyl)oxy]benzamide (0.912 g, 1.80 mmol), EDCI (0.69 g, 3.6 mmol), N,N-diisopropylethylamine (0.466 g, 3.6 mmol), and N,N-dimethylglycine (0.372 g, 3.6 mmol) in methylene chloride (17 mL) was stirred overnight at room temperature. The reaction was diluted with water, washed with brine, dried (Na2SO4), and concentrated. The residue was purified by flash chromatography on silica gel (8%-10% MeOH:CH2Cl2) to give the title compound (0.515 g, 48%) as a pale yellow solid. MS (ES+) m/e 592 [M+H]+.

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel (8%-10% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-bf0940b02d5445768406a6259a1f92b1
Source dataset
uspto-grants-2012_04
Patent number
US08163919B2

Reaction notes

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