Pyridine → 2-(4-pyridin-3-yl-1,3-thiazol-2-yl)-1H-benzimidazole-4-carboxamide

HRID 564216Notes

Reaction equation

N1C=CC=[C:3]([C:7]2[S:8][CH:9]=[C:10](C(O)=O)[N:11]=2)C=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[NH2:29][C:30]1[C:38]([NH2:39])=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH2:34])=[O:33].[N:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C>[N:40]1[CH:45]=[CH:44][CH:43]=[C:42]([C:10]2[N:11]=[C:7]([C:3]3[NH:39][C:38]4[CH:37]=[CH:36][CH:35]=[C:31]([C:32]([NH2:34])=[O:33])[C:30]=4[N:29]=3)[S:8][CH:9]=2)[CH:41]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of 2-(3-pyridyl)-1,3-thiazole-4-carboxylic acid (300 mg) in pyridine (5 mL) and DMF (5 mL) at ambient temperature was added CDI (248 mg). The mixture was heated at 40° C. for 2 hours, treated with 2,3-diaminobenzamide dihydrochloride (326 mg), stirred at ambient temperature for 16 hours and concentrated. The concentrate was heated in glacial acetic acid (20 mL) at 110° C. for 2 hours, cooled and concentrated. The concentrate was partitioned between ethyl acetate and sodium bicarbonate solution, and the solid that precipitated was filtered and washed with water and ethyl acetate. 1H NMR (DMSO-d6) δ 7.38 (t, J=7.8 Hz, 1H), 7.60-7.67 (m, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.81 (brs, 1H), 7.90 (dd, J=7.46, 1.0 Hz, 1H), 8.44-8.50 (m, 1H), 8.74-8.76 (m, 1H), 8.74 (s, 1H), 9.29 (brs, 1H), 9.34 (d, J=1.7 Hz, 1H), 13.44 (brs, 1H).

Workup

concentrationconcentrated
temperatureThe concentrate was heated in glacial acetic acid (20 mL) at 110° C. for 2 hours
temperaturecooled
concentrationconcentrated
customThe concentrate was partitioned between ethyl acetate and sodium bicarbonate solution
customthe solid that precipitated
filtrationwas filtered
washwashed with water and ethyl acetate

Sources & evidence

ORD record: ord-6b31889c129843c59b098b6eaacdf351
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067613B2

Reaction notes

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