(R)-(-)-2-Amino-1-phenylethanol → (R)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(2-hydroxy-2-phenylethyl)isonicotinamide

HRID 714364Notes

Reaction equation

HRID 714364 reaction equation
O1C=C(CN)N=C1.[NH2:8][CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11].[F:18][C:19]1[CH:40]=[CH:39][C:22]([CH2:23][N:24]2[CH2:28][CH2:27][N:26]([C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][N:37]=3)[C:32](O)=[O:33])[C:25]2=[O:38])=[CH:21][CH:20]=1>>[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][N:24]2[CH2:28][CH2:27][N:26]([C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][N:37]=3)[C:32]([NH:8][CH2:9][C@H:10]([OH:11])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:33])[C:25]2=[O:38])=[CH:39][CH:40]=1

Participants

4

Reactant 3

HCID 6951165(R)-(-)-2-Amino-1-phenylethanolHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44552913(R)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(2-hydroxy-2-phenylethyl)isonicotinamideYield 49%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (R)-2-amino-1-phenylethanol to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, (R)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(2-hydroxy-2-phenylethyl)isonicotinamide was obtained as a colorless solid in 49% yield: mp 97-99° C.; 1H NMR (300 MHz, CDCl3) δ 8.49 (s, 1H), 8.32 (d, J=5.4 Hz, 1H), 7.65 (br s, 1H), 7.39-7.16 (m, 8H), 7.02-6.96 (m, 2H), 5.00 (d, J=6.9 Hz, 1H), 4.36-4.27 (m, 3H), 4.03-3.87 (m, 3H), 3.46-3.31 (m, 3H); 13C NMR (75 MHz, CDCl3) δ 166.7, 164.0, 160.8, 156.9, 152.6, 148.0, 143.2, 141.9, 131.9, 131.9, 129.9, 129.8, 128.5, 127.8, 125.8, 116.2, 115.9, 115.6, 109.5, 48.1, 47.2, 41.4, 41.0; MS (ES+) m/z 434.7 (M+1).

Sources & evidence

ORD record
ord-c2cae38aefc54ecaa6d441350b693d81
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

Loading…