Calcium Carbonate → HCID 66860039, compound

HRID 1803277Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:18]=[C:17]4[C:19]5([CH2:25][CH2:26][CH2:27][CH2:28][N:16]4[N:15]=3)SCCCS5)=[CH:9][C:8]=2[O:29][CH3:30])[CH:6]=1.C(=O)([O-])[O-:32].[Ca+2]>C(#N)C.O.CCOC(C)=O.[Hg](Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:18]=[C:17]4[C:19](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][N:16]4[N:15]=3)=[CH:9][C:8]=2[O:29][CH3:30])[CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-5,6,7,8-tetrahydrospiro[[1,2,4]triazolo[1,5-a]azepine-9,2′-[1,3]dithian]-2-amine (80 mg, 0.173 mmol) in acetonitrile (1.5 mL) and water (0.4 mL) was added calcium carbonate (51.9 mg, 0.518 mmol) and mercury(II) chloride (141 mg, 0.518 mmol). The mixture was stirred at 80° C. for 5 h and at 100° C. for 6 h. The crude reaction was diluted with EtOAc (150 mL) and washed with aqueous solution of ammonium acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-7,8-dihydro-5H-[1,2,4]triazolo[1,5-a]azepin-9(6H)-one (28 mg, 0.075 mmol, 44% yield). LC-MS (M+H)+ =373.1. The crude product was used in the next step without purification.

Workup

customThe crude reaction
washwashed with aqueous solution of ammonium acetate
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3f5311a522b740f1b0f19315f1db0bf4
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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