Dimethylformamide → HCID 178444543, compound

HRID 842731Notes

Reaction equation

HRID 842731 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[CH3:16][N:17]([CH3:26])[CH2:18][CH2:19][CH2:20][N:21]=[C:22]=[N:23][CH2:24][CH3:25].O.ON1C2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2N=N1.[CH2:38]([N:40]([CH2:43]C)CC)C.[CH3:45][N:46](C=O)C>>[C:45]([C:36]1[CH:35]=[CH:34][C:25]([CH2:24][N:23]2[C:19]([CH2:18][N:17]3[CH2:16][CH2:43][N:40]([C:12]([C@H:9]4[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]4)=[O:14])[CH2:38][CH2:26]3)=[CH:20][N:21]=[CH:22]2)=[CH:32][CH:37]=1)#[N:46]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178444557HCID 178444557, compound

Product 1

HCID 178444543HCID 178444543, compound

Procedure

Trans-4-pentylcyclohexane carboxylic acid (0.4 mmol) and 1-(4-cyanobenzyl)-5-(1H-piperazin-4-yl)methylimidazole prepared as described in Example 2, step 2 (0.36 mmol) were dissolved in DMF (1 mL) and then 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.44 mmol), 1-Hydroxybenzotriazole hydrate (0.44 mmol) and triethylamine (1.44 mmol) were added. The reaction stirred overnight at room temperature, was run through a glass syringe filter and purified by preparative HPLC. The product was converted to the Bis-hydrochloride salt by exposure of a dichloromethane solution of the product to excess ethereal HCl. Concentration in vacuo provided the title compound as a white powder (68 mg).1H-NMR (CD3OD): 9.06 (s, 1H); 7.89 (s, 1H); 7.83 (d, 2H); 7.51 (d, 2H); 5.76 (s, 2H); 4.1 (m, 2H); 3.7 (m, 4H); 2.93 (m, 4H); 2.59 (t, 1H); 1.81 (d, 2H); 1.73 (d, 2H); 1.41 (q, 2H); 1.2-1.4 (m, 9H); 1.05 (q, 2H); 0.88 (t, 3H). MS: found 462.4 (M+H).

Workup

  1. customwas run through a glass syringe
  2. filtrationfilter
  3. custompurified by preparative HPLC
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-458403e118894635900d98725cdd206d
Source dataset
uspto-grants-2002_04
Patent number
US06376496B1

Reaction notes

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