2-(2,6-Dioxo-3-piperidyl)-4-(2-methoxyethylamino)isoindoline-1,3-dione → 2-(2,6-Dioxo-piperidin-3-yl)-4-[(thiophen-2-ylmethyl)-amino]-isoindole-1,3-dione

HRID 2103557

反応式

HRID 2103557 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:10]([C:11]([OH:13])=O)[C:9]=1[C:17]([OH:19])=O.[O:20]=[C:21]1[CH:26]([N:27]2C(=O)C3C(=CC=CC=3NCCOC)C2=O)[CH2:25][CH2:24][C:23](=[O:43])[NH:22]1>>[O:20]=[C:21]1[CH:26]([N:27]2[C:17](=[O:19])[C:9]3[C:10](=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][CH2:6][C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[C:11]2=[O:13])[CH2:25][CH2:24][C:23](=[O:43])[NH:22]1

参加物

3

反応物 2

HCID 99236092-(2,6-Dioxo-3-piperidyl)-4-(2-methoxyethylamino)isoindoline-1,3-dioneHCID 219885963-[(Thiophen-2-ylmethyl)-amino]-phthalic acid

生成物 1

HCID 219885972-(2,6-Dioxo-piperidin-3-yl)-4-[(thiophen-2-ylmethyl)-amino]-isoindole-1,3-dione収率 29%

実験手順

3-[(Thiophen-2-ylmethyl)-amino]-phthalic acid (2.88 mmol) was treated in the same manner as described above for the synthesis of 2-(2,6-dioxo-piperidin-3-yl)-4-(2-methoxy-ethylamino)-isoindole-1,3-dione. The solid yellow residue was purified by preparative HPLC (Symmetry C18, isocratic, 35% acetonitrile/water) to give 0.31 g (29%) of product as a yellow solid: mp 223-225° C.; 1H NMR (DMSO-d6) δ 11.12 (s, 1H), 7.56 (t, J=7.8 Hz, 1H), 7.39 (d, J=4.8 Hz, 1H), 7.23-6.96 (m, 5H), 5.07 (dd, J=5.3 and 12.4 Hz, 1H), 4.75 (d, J=6.0 Hz, 2H), 2.97-2.83 (m, 1H), 2.63-2.46 (m, 2H), 2.09-1.99 (m, 1H); 13C NMR (DMSO-d6) δ 172.77, 170.03, 168.67, 167.20, 145.60, 142.51, 136.04, 132.15, 126.88, 125.40, 125.00, 117.67, 111.05, 109.80, 48.56, 40.88, 30.96, 22.10; Anal. Calcd. For C18H15N3O4S: C, 58.53; H, 4.09; N, 11.38. Found: C, 58.20; H, 3.96; N, 10.99.

後処理

  1. customThe solid yellow residue was purified by preparative HPLC (Symmetry C18, isocratic, 35% acetonitrile/water)

出典と根拠

ORDレコード
ord-f99fa60710d2401db8c72d5e55931c84
出典データセット
uspto-grants-2009_08
特許番号
US07576104B2

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