Hydrochloric Acid → HCID 178436773, compound

HRID 1509056Notes

Reaction equation

Cl[C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([CH3:10])[N:5]=[C:4]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[N:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[NH:26][CH:27]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[N:29]=2)=[CH:20][CH:19]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1.CC(O)=O>[Cl:16][C:13]1[S:12][C:11]([C:4]2[N:3]=[C:2]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:24][C:25]4[NH:26][CH:27]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[N:29]=4)=[CH:22][CH:23]=3)[C:7]([CH2:8][CH3:9])=[C:6]([CH3:10])[N:5]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A 8-mL vial was charged with 4-chloro-2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidine (100 mg, 0.366 mmol, 1.05 eq.), methyl 2-[(4-aminophenyl)methyl]-1H-imidazole-4-carboxylate (81 mg, 0.348 mmol, 1 eq.), AcOH (0.8 ml). To the mixture was added 4N HCl in dioxane (4 drops using 1 ml of a syringe). The resulting mixture was stirred under 110° C. for 2 hrs. After cooling to room temperature, the mixture was added to sodium bicarbonate solution (20 ml). The precipitate was collected by filtration and washed with water then purified by chromatography on silica gel using 1˜1.5% of methanol in dichloromethane as eluent to give the title compound as a foam (79 mg, 48% yield).). MW=467.97. 1H NMR (400 MHz, CDCl3) δ 7.65 (m, 4H), 7.30 (m, 2H), 6.93 (d, J=3.6 Hz, 1H), 6.54 (brs, 1H), 4.18 (s, 2H), 3.90 (s, 3H), 2.64 (q, J=6.8 Hz, 2H), 2.49 (s, 3H), 1.26 (t, J=6.8 Hz, 3H).

Workup

temperatureAfter cooling to room temperature
filtrationThe precipitate was collected by filtration
washwashed with water
customthen purified by chromatography on silica gel using 1˜1.5% of methanol in dichloromethane as eluent

Sources & evidence

ORD record: ord-c318343e57ac48ffbeaaf22ab7f70c20
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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