4-(Morpholin-4-ylsulphonyl)benzeneboronic acid → 1-[4-(Morpholine-4-sulfonyl)-phenyl]-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029140Notes

Reaction equation

HRID 1029140 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.B([C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1)(O)O>>[N:29]1([S:26]([C:23]2[CH:24]=[CH:25][C:20]([C:2]3[CH:11]=[CH:10][N:9]=[C:8]4[C:3]=3[C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[C:6](=[O:12])[NH:7]4)=[CH:21][CH:22]=2)(=[O:27])=[O:28])[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1

Participants

3

Reactant 2

HCID 441195464-(Morpholin-4-ylsulphonyl)benzeneboronic acidHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 581679971-[4-(Morpholine-4-sulfonyl)-phenyl]-5H-benzo[c][1,8]naphthyridin-6-oneYield 80%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 171 using Compound 83 (100 mg, 0.43 mmol) and 4-(4-boronobenzenesulfonyl)morpholine (235 mg, 0.87 mmol) to provide 176 (145 mg, 79% yield) as a grey solid. LC-MS (M+H=422, obsd.=422).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-f6d5ba3001354120b1f4f5769e46446f
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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