Pipemidic Acid → 2-(4-{[(3-Chlorophenyl)amino]carbonothioyl}-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid

HRID 455926

反応式

HRID 455926 の反応式
[CH3:1][CH2:2][N:3]1[C:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:12]=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1.[Cl:23][C:24]1[CH:25]=[C:26]([N:30]=[C:31]=[S:32])[CH:27]=[CH:28][CH:29]=1.C(N(CC)CC)C>>[Cl:23][C:24]1[CH:25]=[C:26]([NH:30][C:31]([N:17]2[CH2:18][CH2:19][N:14]([C:11]3[N:12]=[CH:13][C:8]4[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4][N:3]([CH2:2][CH3:1])[C:9]=4[N:10]=3)[CH2:15][CH2:16]2)=[S:32])[CH:27]=[CH:28][CH:29]=1

参加物

4

反応物 3

HCID 4831Pipemidic AcidHCID 8471TriethylamineHCID 754493-Chlorophenyl isothiocyanate

生成物 1

HCID 454841482-(4-{[(3-Chlorophenyl)amino]carbonothioyl}-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid

実験手順

Pipemidic acid (25 mg, 0.0824 mmol), 3-chlorophenyl isothiocyanate (11 μL, 0.0824 mmol) and triethylamine (23 μL, 0.165 mmol) were used. Purification on silica yielded compound 14 in Table 1, below (8.2 mg, 21%). 1H NMR (300 MHz, CDCl3) δ 9.03 (s, 1H), 8.51 (s, 1H), 7.10 (s, 1H), 7.04-6.93 (m, 2H), 6.90-6.84 (m, 1H), 4.14 (q, J=6.90 Hz, 2H), 4.00-3.74 (m, 8H), 1.23 (t, J=7.01 Hz, 3H) ppm.

後処理

  1. customPurification on silica yielded compound 14 in Table 1

出典と根拠

ORDレコード
ord-6ccf6c182d494436a11b17d86190a189
出典データセット
uspto-grants-2013_07
特許番号
US08497371B2

関連ノート

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