Dimethylacetamide → HCID 59349405, compound

HRID 415052Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[N:13]=[CH:14][NH:15][C:16]=1[C:17]([NH:19][C:20]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([O:29][CH2:30][C:31](OCC)=[O:32])=[CH:28][C:22]=2[N:21]=1)=[O:18])=[O:11].[NH2:36][CH2:37][CH:38]([OH:41])[CH2:39][OH:40].CC(N(C)C)=O>C1COCC1>[OH:41][CH:38]([CH2:39][OH:40])[CH2:37][NH:36][C:31](=[O:32])[CH2:30][O:29][C:27]1[CH:26]=[CH:25][C:23]2[N:24]=[C:20]([NH:19][C:17]([C:16]3[NH:15][CH:14]=[N:13][C:12]=3[C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])=[O:11])=[O:18])[NH:21][C:22]=2[CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a seal tube was added ethyl 2-(2-(4-(2,4-dimethylphenylcarbamoyl)-1H-imidazole-5-carboxamido)-1H-benzo[d]imidazol-5-yloxy)acetate (230 mg, 0.5 mmol), 3-aminopropane-1,2-diol (180 mg, 2 mmol), DMA (3 mL) and THF (3 mL), the mixture was heated to 90° C. overnight. The reaction was allowed to cool to room temperature, concentrated under reduced pressure and purified by preparative reverse phase HPLC (aqueous ammonium acetate—acetonitrile) to give 64 mg of N5-[6-({2-[(2,3-dihydroxypropyl)amino]-2-oxoethyl}oxy)-1H benzimidazol-2-yl]-N4-(2,4-dimethylphenyl)-1H-imidazole-4,5-dicarboxamide as the desired product. 1H-NMR (DMSO-d6) δ 8.05 (s, 1H), 7.68 (d, 2H), 7.43 (s, br 2H), 7.05 (dd, 2H), 6.93 (d, 2H), 4.31 (m, 1H), 2.65 (m, 2H), 2.29 (q, 2H), 2.14 (m, 2H), 1.88 (m, 2H), 1.59 (m, 2H), 0.95 (t, 3H). MS (EI): 474 (MH+).

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
custompurified by preparative reverse phase HPLC (aqueous ammonium acetate—acetonitrile)

Sources & evidence

ORD record: ord-8a55aecb1b15451ba90cbc71835ea563
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088767B2

Reaction notes

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