Potassium Carbonate → HCID 57590535, compound

HRID 1783486Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23](I)=[CH:22][C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([SH:37])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>C(O)(C)C.CO.C(Cl)Cl.[Cu]I>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23]([S:37][C:27]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:30]=[CH:29][CH:28]=4)=[CH:22][C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-(5-iodobenzoxazol-2-yl)piperazine-1-carboxylic acid benzyl ester, prepared in Example 2 (1.48 mmol theory), 1-napthalenethiol (0.237 g, 1.48 mmol), CuI (0.042 g, 0.22 mmol), and K2CO3 (0.409 g, 2.96 mmol) in isopropanol was heated at 90° C. overnight, diluted with 20% MeOH in CH2Cl2, and filtered through a pad of silica gel. The filtrate was concentrated to dryness. The resultant residue was purified by chromatography with 5% MeOH in CH2Cl2 to provide the title compound (230 mg, 31% overall yield from 4-benzoxazol-2-yl-piperazine-1-carboxylic acid benzyl ester), characterized by NMR and mass spectral analyses.

Workup

filtrationfiltered through a pad of silica gel
concentrationThe filtrate was concentrated to dryness
customThe resultant residue was purified by chromatography with 5% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-8b005d31478d4b1bb3a11fdf7a2d4054
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501421B2

Reaction notes

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