Acetic Acid → HCID 44177562, compound

HRID 341164Notes

Reaction equation

HRID 341164 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[N:15]3[CH:16]=[CH:17][C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)[CH:21]=4)=[CH:19][C:14]3=[N:13][CH:12]=2)[CH:10]=1)[C:5]([NH2:7])=[O:6].[CH3:33][C:34](O)=[O:35].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:34]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[N:15]3[CH:16]=[CH:17][C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][N:27]5[CH2:28][CH2:29][O:30][CH2:31][CH2:32]5)[CH:21]=4)=[CH:19][C:14]3=[N:13][CH:12]=2)[CH:10]=1)[C:5]([NH2:7])=[O:6])(=[O:35])[CH3:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59321103HCID 59321103, compound

Product 1

HCID 44177562HCID 44177562, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-Amino-5-[7-(3-morpholin-4-ylmethyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzamide (90 mg), AcOH (29 μL, 0.5 mmol), 1-hydroxybenzotriazole (68 mg, 0.5 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (96 mg, 0.5 mmol) in dry DMF (2 ml) was stirred at RT under N2 for 24 h. The mixture was partitioned between CH2Cl2/H2O. The layers were separated and the aqueous layer was loaded on to a SCX cartridge. This was washed with MeOH, then 2M NH3-MeOH. The NH3-MeOH fraction was evaporated and the residue was purified by preparative HPLC to give the title compound (40 mg, solid). 1H NMR (400 MHz, DMSO-d6): 10.26 (1H, s), 8.68 (1H, d), 8.12 (1H, s), 8.07 (2H, brs), 7.99 (1H, s), 7.87 (1H, s), 7.83 (1H, s), 7.81-7.72 (2H, m), 7.54-7.43 (2H, m), 7.43-7.34 (2H, m), 3.66-3.54 (6H, m), 2.47-2.36 (4H, m), 2.11 (3H, s).

Workup

  1. customThe mixture was partitioned between CH2Cl2/H2O
  2. customThe layers were separated
  3. washThis was washed with MeOH
  4. customThe NH3-MeOH fraction was evaporated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-47456f0470d74329b6161d8935d56dfd
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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