4-Hydroxybenzoic Acid → HCID 21264383、化合物

HRID 567107ノート

反応式

HRID 567107 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]2[C:45]3[CH:46]=[CH:47][S:48][C:44]=3[CH2:43][CH2:42][NH:41]2)=[CH:36][CH:35]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[Cl:33][C:34]1[CH:35]=[CH:36][C:37]([CH:40]2[C:45]3[CH:46]=[CH:47][S:48][C:44]=3[CH2:43][CH2:42][N:41]2[C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=2)=[O:8])=[CH:38][CH:39]=1

参加物

8

反応物 5

HCID 1354-Hydroxybenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27392694-(4-Chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

生成物 1

HCID 21264383HCID 21264383、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

4-Hydroxybenzoic acid (1.3 g, 9.6 mmol) was dissolved in N,N-dimethylformamide (25 ml) and 1-hydroxybenzotriazole (1.3 g, 9.6 mmol) was added followed by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.8 g, 9.6 mmol), 4-(4-chlorophenyl)4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (2.0 g, 8 mmol) and N,N-diisopropylethylamine (2.5 ml, 16 mmol). The resulting mixture was stirred at room temperature for 16 hours. Water (200 ml) was added and the mixture was extracted with diethyl ether (3×100 ml). The combined organic extracts were washed with saturated aqueous sodium chloride (150 ml), dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography over silica gel eluting with a mixture of ethyl acetate and heptane (1:1). The pure fractions were pooled and concentrated in vacuo to afford 3.14 9 (100%) of the title compound.

後処理

  1. extractionthe mixture was extracted with diethyl ether (3×100 ml)
  2. washThe combined organic extracts were washed with saturated aqueous sodium chloride (150 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography over silica gel eluting with a mixture of ethyl acetate and heptane (1:1)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7e64be5d74ec4b959497cad2b84ace18
出典データセット
uspto-grants-2001_01
特許番号
US06177443B1

反応ノート

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