Dimethylformamide → HCID 178497576, compound

HRID 711317

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:13]2[NH:12][C:11]([C:14]3[C:15](=[O:21])[NH:16][CH:17]=[CH:18][C:19]=3Cl)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[NH2:22][CH2:23][C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25].CN1CCOCC1.CN(C=O)C>O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[NH:12][C:11]([C:14]3[C:15](=[O:21])[NH:16][CH:17]=[CH:18][C:19]=3[NH:22][CH2:23][C@@H:24]([OH:25])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 85 °C

Procedure

In a 40 mL vial, 2-(4-chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-3H-benzoimidazole-4-carboxylic acid methyl ester (0.91 g, 3.00 mmol), (S)-2-amino-1-phenylethanol (822 mg, 5.99 mmol) and N-methylmorpholine (909 mg, 988 μL, 8.99 mmol) were combined with DMF (20 mL) to give a black suspension. The vial was sealed and heated in a dry block at 85° C. for 6.5 hr and allowed to cool to room temperature over the weekend. The reaction was diluted with water and the resulting precipitate was washed with water and hexanes yielding 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid methyl ester (0.87 g, 71.8% yield) as a light purple solid. LC/MS calcd for C22H20N4O4 (m/e) 404.0, obsd 405.2 (M+H); 1H NMR (DMSO-d6): 13.53 (s, 1H), 11.26 (d, J=5.8 Hz, 1H), 10.85 (t, J=5.1 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.76-7.82 (m, 1H), 7.55 (d, J=7.3 Hz, 2H), 7.34-7.42 (m, 3H), 7.26-7.34 (m, 2H), 6.22 (d, J=7.5 Hz, 1H), 5.80 (d, J=4.5 Hz, 1H), 4.85-5.00 (m, 1H), 3.98 (s, 3H), 3.64-3.77 (m, 1H), 3.53-3.63 (m, 1H).

Workup

customto give a black suspension
customThe vial was sealed
temperatureto cool to room temperature over the weekend
washthe resulting precipitate was washed with water and hexanes

Sources & evidence

ORD record: ord-0a59aa8861344c9e94c60507205b06dd
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181218B2

Linked notes

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