Potassium Phosphate, Tribasic → HCID 24825878, compound

HRID 910918Notes

Reaction equation

HRID 910918 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[Cl:8][C:9]1[CH:14]=[C:13]([S:15][C:16]2[N:17]([CH3:21])[CH:18]=[CH:19][N:20]=2)[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].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>[ClH:8].[ClH:8].[CH3:21][N:17]1[CH:18]=[CH:19][N:20]=[C:16]1[S:15][C:13]1[CH:14]=[CH:9][N:10]=[C:11]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 637784912-Chloro-4-[(1-methyl-1H-imidazol-2-yl)thio]pyridine

Product 1

HCID 24825878HCID 24825878, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (11.21 mL, 4.484 mmol), 2-chloro-4-(1-methyl-1H-imidazol-2-ylthio)pyridine (1.012 g, 4.484 mmol), potassium phosphate (0.9518 g, 4.484 mmol), Pd2(dba)3 (0.09332 g, 0.1019 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.06486 g, 0.1121 mmol) were reacted to provide 4-(1-methyl-1H-imidazol-2-ylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine dihydrochloride (0.676 g, 44.07% yield) after salt formation. 1H NMR (d6-DMSO) δ 8.25 (d, 1H), 8.04 (d, 1H), 7.88 (d, 1H), 6.87 (s, 1H), 6.83 (dd, 1H), 6.70 (d, 1H), 3.83 (s, 3H), 2.26 (s, 3H); Mass spectrum (apci) m/z=304.1 (M+H-2HCl).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8b1040c5cf24427ebb8fe5326f38bae3
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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