Hydrochloric Acid → 3-(benzyloxy)-5-(1-methyl-1H-imidazol-2-ylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine dihydrochloride

HRID 1426178Notes

Reaction equation

HRID 1426178 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH3:22])[N:21]=2)=[N:11][CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(N(C(C)C)C(C)C)C.[CH3:74][N:75]1[CH:79]=[CH:78][N:77]=[C:76]1[SH:80].[ClH:81]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[ClH:81].[ClH:81].[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH3:22])[N:21]=2)=[N:11][CH:12]=[C:13]([S:80][C:76]2[N:75]([CH3:74])[CH:79]=[CH:78][N:77]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16061466HCID 16061466, compoundHCID 178480602HCID 178480602, compound

Product 1

HCID 866397063-(benzyloxy)-5-(1-methyl-1H-imidazol-2-ylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine dihydrochlorideYield 49%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.125 g, 0.332 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0192 g, 0.0332 mmol), Pd2dba3 (0.0152 g, 0.0166 mmol), N-ethyl-N-isopropylpropan-2-amine (0.116 ml, 0.664 mmol), 1-methyl-1H-imidazole-2-thiol (0.0379 g, 0.332 mmol) were reacted according to Example 42 to provide 3-(benzyloxy)-5-(1-methyl-1H-imidazol-2-ylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine dihydrochloride (0.0786 g, 49.0% yield) after HCl salt formation. 1H NMR (DMSO-d6) δ 8.16 (d, 1H), 7.81 (d, 1H), 7.78 (s, 1H), 7.73 (d, 1H), 7.53 (d, 2H), 7.41-7.34 (m, 3H), 6.74 (s, 1H), 5.31 (s, 2H), 3.85 (s, 3H), 2.46 (s, 3H). Mass spectrum (apci) m/z=410.0 (M+H-2HCl).

Sources & evidence

ORD record
ord-038401c4057d479f933efecfed33c058
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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