Thiazole → 2-Amino-N-(5-phenoxy-thiophen-2-ylmethyl)-6-thiazol-2-yl-nicotinamide

HRID 2080193Notes

Reaction equation

[NH2:1][C:2]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].C1C=CC(CC(NCN[C@H](C(O)=O)CC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1.[S:51]1[CH:55]=[CH:54][N:53]=[CH:52]1>C1(C)C(C)=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:23]=[C:22]([C:52]2[S:51][CH:55]=[CH:54][N:53]=2)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (101 mg, 0.281 mmol) in xylene (7 mL) were added 2-tributylstanyl thiazole (137 mg, 0.365 mmol) and tetrakis(triphenylphosphine)palladium(0) (81 mg, 0.070 mmol) under nitrogen atmosphere, and the solution was stirred for 12 hours at 120° C. The reaction mixture was concentrated, the obtained residue was purified by silica gel chromatography (toluene-ethyl acetate), then, the obtained residue was washed by hexane-ethyl acetate (20:1), and the title compound (22 mg, 0.054 mmol, 19%) was obtained.

Workup

concentrationThe reaction mixture was concentrated
customthe obtained residue was purified by silica gel chromatography (toluene-ethyl acetate)
washthe obtained residue was washed by hexane-ethyl acetate (20:1)

Sources & evidence

ORD record: ord-af4a68b7e92e4dcd98c2b13bd1cec01f
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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