Hydrochloric Acid → HCID 59569046, compound

HRID 1517185Notes

Reaction equation

HRID 1517185 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([CH3:13])[C:11]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]([CH3:24])[S:22][C:21](=[O:25])[N:20]([CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)[N:19]=4)=[CH:17][C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1>[NH2:28][CH2:27][CH2:26][N:20]1[N:19]=[C:18]([C:16]2[CH:15]=[CH:14][C:11]3[N:12]([CH3:13])[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)=[N:9][C:10]=3[CH:17]=2)[CH:23]([CH3:24])[S:22][C:21]1=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59569058HCID 59569058, compound

Product 1

HCID 59569046HCID 59569046, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6.3 g (13 mM) of tert-butyl 2-[5-[2-(3-fluorophenyl)-1-methyl-1H-benzimidazol-5-yl]-6-methyl-2-oxo-2H-1,3,4-thiadiazin-3(6H)-yl]ethylcarbamate are added to 30 ml of 4N hydrochloric dioxane. The mixture is stirred at room temperature for 20 hours. The crystalline solid, which is the hydrochloride of the desired compound, is filtered off. The free base is obtained via the action of aqueous sodium hydrogen carbonate solution and extraction with ethyl acetate. The aqueous phase is washed with water and then dried over sodium sulfate and concentrated under vacuum to give 3.85 g of 3-(2-aminoethyl)-5-[2-(3-fluorophenyl)-1-methyl-1H-benzimidazol-5-yl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in solid form.

Sources & evidence

ORD record
ord-2040f5781b8445319ac66986d95747f9
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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