Benzyl 4-(bromomethyl)piperidine-1-carboxylate → 2-(2,6-Difluorophenyl)-5-(4-(piperidin-4-ylmethoxy)phenyl)oxazole-4-carboxamide

HRID 715003Notes

Reaction equation

HRID 715003 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[C:12]([C:14]([NH2:16])=[O:15])[N:13]=1.Br[CH2:25][CH:26]1[CH2:31][CH2:30][N:29](C(OCC2C=CC=CC=2)=O)[CH2:28][CH2:27]1.COC1C=CC(C2NC(C(N)=O)=C(C3C=CC(OC)=CC=3)N=2)=CC=1>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:25][CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:21][CH:22]=2)=[C:12]([C:14]([NH2:16])=[O:15])[N:13]=1

Participants

6

Reactant 3

HCID 2776274Benzyl 4-(bromomethyl)piperidine-1-carboxylateHCID 595874242,4-bis(4-methoxyphenyl)-1H-imidazole-5-carboxamideHCID 595875782-(2,6-Difluorophenyl)-5-(4-hydroxyphenyl)oxazole-4-carboxamide

Product 1

HCID 595874752-(2,6-Difluorophenyl)-5-(4-(piperidin-4-ylmethoxy)phenyl)oxazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared by alkylation of 2-(2,6-difluorophenyl)-5-(4-hydroxyphenyl)oxazole-4-carboxamide with benzyl 4-(bromomethyl)piperidine-1-carboxylate according to the procedure described in example S-1, step b, followed by subsequent deprotection using the H-cube hydrogenation system (full H2 mode, 10% Pd\C catalyst, 1 ml/min, 20° C., 0.05M in MeOH). NMR (DMSO) δ 1.30-1.50 (2H, m), 1.85 (2H, d), 1.90-2.10 (1H, m), 2.71-2.81 (2H, m), 3.21 (2H, d), 3.92 (2H, d), 7.05-7.15 (2H, m), 7.35-7.45 (2H, m), 7.60-7.80 (3H, m), 8.21-8.30 (2H, m). LCMS (2) 3.13 min; m/z (ES+) 414.

Sources & evidence

ORD record
ord-851555c67e5a4352b5d94e545d1cf7d6
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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