1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69070759, compound

HRID 2111810Notes

Reaction equation

HRID 2111810 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20](O)=[O:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].CCN=C=[N:27][CH2:28][CH2:29][CH2:30][N:31]([CH3:33])C.[CH:34]1C=CC2N(O)N=NC=2[CH:39]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]([NH:27][CH2:28][C:29]4[CH:30]=[N:31][CH:33]=[CH:34][CH:39]=4)=[O:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 69069868HCID 69069868, compound

Product 1

HCID 69070759HCID 69070759, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred mixture of 1-[3-(acetylamino)phenyl]-1H-benzimidazole-5-carboxylic acid (0.83 g, 2.8 mmol), EDCI (0.81 g, 4.22 mmol), HOBt (0.57 g, 4.22 mmol) in anhydrous DMA (10 mL) was added DIPEA (0.75 mL, 4.31 mmol) at rt. The reaction mixture was stirred for 0.5 h and then (3-aminomethyl)pyridine (0.57 mL, 5.62 mmol) was added drop-wise. Stirring was continued for an additional 25 h. The solvent was evaporated in vacuo and the crude material was purified by silica gel chromatography (5%-15% MeOH in CH2Cl2) and then recrystallized from acetone to afford 1-[3-(acetylamino)phenyl]-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 2.09 (3H, s), 4.54 (d, J=6.0 Hz, 2H), 7.35-7.40 (m, 2H), 7.56 (t, J=8.0 Hz, 1H), 7.62 (d, J=7.6 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.92 (dd, J=8.4 Hz, 1.2 Hz, 1H), 8.04 (t, J=2.0 Hz, 1H), 8.38 (d, J=1.2 Hz, 1H), 8.46 (dd, J=4.8 Hz, 1.6 Hz, 1H), 8.58 (1H, J=1.6 Hz, 1H), 8.68 (s, 1H), 9.21 (t, J=5.6 Hz, 1H), 10.33 (s, 1H). MS (ES+): m/z 386 [MH+].

Workup

  1. stirringStirring
  2. waitwas continued for an additional 25 h
  3. customThe solvent was evaporated in vacuo
  4. customthe crude material was purified by silica gel chromatography (5%-15% MeOH in CH2Cl2)
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-df5ccd037225487fa31f925c81ae77f8
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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