(2-Oxo-1,2-dihydroquinolin-3-yl)boronic acid → HCID 136341349, compound

HRID 579370Notes

Reaction equation

HRID 579370 reaction equation
[O:1]=[C:2]1[C:11](B(O)O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.Br[C:16]1[S:20][C:19]([N:21]([CH3:32])[CH:22]2[CH2:27][C:26]([CH3:29])([CH3:28])[NH:25][C:24]([CH3:31])([CH3:30])[CH2:23]2)=[N:18][N:17]=1>>[CH3:32][N:21]([CH:22]1[CH2:27][C:26]([CH3:29])([CH3:28])[NH:25][C:24]([CH3:31])([CH3:30])[CH2:23]1)[C:19]1[S:20][C:16]([C:11]2[C:2](=[O:1])[NH:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[N:17][N:18]=1

Participants

3

Reactant 2

HCID 49757966(2-Oxo-1,2-dihydroquinolin-3-yl)boronic acidHCID 867271295-Bromo-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 136341349HCID 136341349, compound

Procedure

Following a similar procedure as described for Step 3 in Example 101, (2-oxo-1,2-dihydroquinolin-3-yl)boronic acid and 5-bromo-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine (858 mg, 2.57 mmol) were reacted to provide the crude product, which was purified by preparative HPLC under basic condition to give 3-(5-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)-1,3,4-thiadiazol-2-yl)quinolin-2(1H)-one (14 mg, MS: 398.2 [M+H+], LCMS Rt=0.51 min (LCMS method D); 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.74 (s, 1H), 7.67-7.80 (m, 1H), 7.47-7.57 (m, 1H), 7.31 (d, J=8.08 Hz, 1H), 7.19-7.27 (m, 1H), 4.34 (br. s., 1H), 2.99 (s, 3H), 1.71 (dd, J=12.63, 3.03 Hz, 2H), 1.50 (t, J=12.38 Hz, 2H), 1.28 (s, 6H), 1.10-1.23 (m, 6H).

Workup

  1. customwere reacted
  2. customto provide the crude product, which
  3. customwas purified by preparative HPLC under basic condition

Sources & evidence

ORD record
ord-9cb155e9a99349cc8c2c6ed3f2bfdf74
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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