4-(Benzylcarbamoyl)benzeneboronic acid → 4'-[({1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-N-(phenylmethyl)-4-biphenylcarboxamide

HRID 423477Notes

Reaction equation

HRID 423477 reaction equation
[C:1]1([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([C:35]3[O:39][N:38]=[C:37]([CH:40]([CH3:42])[CH3:41])[N:36]=3)[CH2:31][CH2:30]2)=[CH:23][CH:22]=1>>[CH3:42][CH:40]([C:37]1[N:36]=[C:35]([N:32]2[CH2:31][CH2:30][CH:29]([CH2:28][O:27][C:24]3[CH:23]=[CH:22][C:21]([C:14]4[CH:15]=[CH:16][C:11]([C:9]([NH:8][CH2:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[O:10])=[CH:12][CH:13]=4)=[CH:26][CH:25]=3)[CH2:34][CH2:33]2)[O:39][N:38]=1)[CH3:41]

Participants

3

Reactant 2

HCID 27732434-(Benzylcarbamoyl)benzeneboronic acidHCID 666732104-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine

Product 1

HCID 591777724'-[({1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-N-(phenylmethyl)-4-biphenylcarboxamideYield 2%

Procedure

The title compound (2 mg, 2%) was prepared from (4-{[(phenylmethyl)amino]carbonyl}phenyl)boronic acid (51 mg, 0.2 mmol) and 4-{[(4-bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine (prepared as in Example 24, Step 1, 76 mg, 0.2 mmol) in a manner similar to Example 1, Step 1, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.83 (d, 2H, J=8.6 Hz), 7.61 (d, 2H, J=8.6 Hz), 7.54 (d, 2H, J=8.9 Hz), 7.39-7.28 (m, 5H), 6.97 (d, 2H, J=8.8 Hz), 6.41 (t, 1H, J=5.7 Hz), 4.68 (d, 2H, J=5.5 Hz), 4.26-4.16 (m, 2H), 3.88 (d, 2H, J=6.4 Hz), 3.18-3.06 (m, 2H), 2.96-2.85 (m, 1H), 2.13-2.01 (m, 1H), 2.02-1.92 (m, 2H), 1.55-1.40 (m, 2H), 1.29 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 511 (M+H).

Sources & evidence

ORD record
ord-7eecc56919c447078dbfa67371363850
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

Loading…