Potassium Phosphate, Tribasic → HCID 24825876, compound

HRID 910914Notes

Reaction equation

HRID 910914 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.Cl[C:9]1[CH:14]=[C:13]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].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>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:9]2[CH:14]=[C:13]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)[CH:12]=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86634717HCID 86634717, compound

Product 1

HCID 24825876HCID 24825876, compoundYield 53.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (18.2 mL, 7.27 mmol), tert-butyl 3-(2-chloropyridin-4-yloxy)piperidine-1-carboxylate (2.50 g, 8.00 mmol), potassium phosphate (1.70 g, 8.00 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.166 g, 0.182 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.116 g, 0.200 mmol) were reacted in toluene (20 mL) and water (5 mL) to provide tert-butyl 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)piperidine-1-carboxylate ((1.70 g, 53.3% yield) as yellow solid. 1H NMR (CDCl3) δ 9.01 (bs, 1H), 8.15 (d, 1H), 6.46 (dd, 1H), 6.36 (s, 2H), 4.30 (m, 1H), 2.94-3.77 (m, 3H), 2.33 (d, 3H), 2.01 (bm, 1H), 1.79 (bm, 3H), 1.52 (m, 1H), 1.39 (bs, 9H); Mass spectrum (apci) m/z=391 (100) (M+H).

Sources & evidence

ORD record
ord-4950f696d4cc48fcb1c3ad4c5bbcbaeb
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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