1,2-Dichloroethane → HCID 69070759, compound

HRID 2111792Notes

Reaction equation

HRID 2111792 reaction equation
CCN(C(C)C)C(C)C.[C:10]([NH:13][C:14]1[CH:15]=[C:16]([N:20]2[C:24]3[CH:25]=[CH:26][C:27]([C:29](O)=[O:30])=[CH:28][C:23]=3[N:22]=[CH:21]2)[CH:17]=[CH:18][CH:19]=1)(=[O:12])[CH3:11].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:46][CH2:47][C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1>CC(N(C)C)=O>[C:10]([NH:13][C:14]1[CH:15]=[C:16]([N:20]2[C:24]3[CH:25]=[CH:26][C:27]([C:29]([NH:46][CH2:47][C:48]4[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=4)=[O:30])=[CH:28][C:23]=3[N:22]=[CH:21]2)[CH:17]=[CH:18][CH:19]=1)(=[O:12])[CH3:11]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 69069868HCID 69069868, compound

Product 1

HCID 69070759HCID 69070759, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

DIPEA (0.75 mL, 4.31 mmol) was added at rt to a mixture of 1-[3-(acetylamino)phenyl]-1H-benzimidazole-5-carboxylic acid (0.83 g, 2.8 mmol), EDC (0.81 g, 4.22 mmol), HOBt (0.57 g, 4.22 mmol) in anhydrous DMA (10 mL). The reaction mixture was stirred for 30 min prior to the dropwise addition of 3-aminomethylpyridine (0.57 mL, 5.62 mmol). After stirring for a further 25 h, the solvent was removed in vacuo and the crude material purified by column chromatography over silica gel eluting with 5-15% MeOH in DCM. The product was further purified by recrystallisation from acetone to afford 1-[3-(acetylamino)phenyl]-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide. 1H NMR (400 MHz, DMSO-d6): δ 2.09 (3H, s), 4.54 (d, J=6.0 Hz, 2H), 7.35-7.4 (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. stirringAfter stirring for a further 25 h
  2. customthe solvent was removed in vacuo
  3. customthe crude material purified by column chromatography over silica gel eluting with 5-15% MeOH in DCM
  4. customThe product was further purified by recrystallisation from acetone

Sources & evidence

ORD record
ord-28118f1c09354bbcbdf5a2cc5dc44001
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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