5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → HCID 86759969, compound

HRID 1794782Notes

Reaction equation

HRID 1794782 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:13])[CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([CH3:12])=[CH:10][CH:11]=1.O=[C:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:34]=[CH:33][C:24]([CH2:25][CH:26]3[S:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1>>[OH:13][C@H:3]([CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([CH3:12])=[CH:10][CH:11]=1)[CH2:2][NH:1][CH:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:34]=[CH:33][C:24]([CH2:25][CH:26]3[S:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])=[CH:23][CH:22]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 69655017HCID 69655017, compound

Product 1

HCID 86759969HCID 86759969, compound

Procedure

The title compound was prepared from (2S)-1-amino-3-[(6-methyl-3-pyridinyl)oxy]-2-propanol (which was obtained in Example 127) and 5-[4-(4-oxo-1-piperidinyl)benzyl]-1,3-thiazolidine-2,4-dione (which was obtained in Example 38) in substantially the same manner, as described in Example 125. The product was obtained as a yellow solid; mp 87° C. (decomposed); 1H NMR (400 MHz, DMSO-d6) δ 1.44–1.49 (m, 2 H), 1.93–1.97 (m, 2 H), 2.38 (s, 3 H), 2.64–2.70 (m, 2 H), 2.77–2.95 (m, 4 H), 3.23–3.27 (m, 1H), 3.35 (brs, 2 H), 3.64–3.67 (m, 2H), 3.93–4.02 (m, 3 H), 4.58–4.62 (m, 1 H), 6.84–6.86 (m, 2 H), 7.03–7.05 (m, 2 H), 7.15–7.17 (m, 1 H), 7.27–7.30 (m, 1 H), 8.14–8.15 (m, 1 H); MS (ES) m/z: 469 (M−H)−.

Workup

  1. customThe product was obtained as a yellow solid

Sources & evidence

ORD record
ord-f9900de547644b0db49f9cdd0f94104d
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

Loading…