Sulfuric Acid → 4-Amino-2-iodo-thieno[3,2-c]pyridine-7-carboxylic acid amide

HRID 1868296ノート

反応式

HRID 1868296 の反応式
[I:1][C:2]1[S:10][C:9]2[C:8]([C:11]#[N:12])=[CH:7][N:6]=[C:5]([NH:13]CC3C=CC(OC)=CC=3)[C:4]=2[CH:3]=1.[OH:23]S(O)(=O)=O>>[NH2:13][C:5]1[C:4]2[CH:3]=[C:2]([I:1])[S:10][C:9]=2[C:8]([C:11]([NH2:12])=[O:23])=[CH:7][N:6]=1

参加物

3

反応物 2

HCID 1118Sulfuric AcidHCID 18446524HCID 18446524、化合物

生成物 1

HCID 569269074-Amino-2-iodo-thieno[3,2-c]pyridine-7-carboxylic acid amide

実験手順

To 2-iodo-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile 27 (3.88 g, 9.21 mmol) was added conc. H2SO4 (9.75 mL). The reaction was stirred for 1 h at room temperature, then quenched by the addition of ice (20 g). The filtered precipitate was washed with H2O, then suspended in 30% MeOH—CH2Cl2 (30 mL). Triethylamine was added dropwise until the solids dissolved. The solution was purified by silica gel column chromatography (eluent: 10 to 20% MeOH in CH2Cl2 with 1% NH4OH additive) to yield 2.6 g of 28. 1H NMR (400 MHz, d6-DMSO) δ 8.46 (s, 1H), 7.94 (m, 2H), 7.31 (bs, 1H), 7.18 (s, 2H).

後処理

  1. customquenched by the addition of ice (20 g)
  2. washThe filtered precipitate was washed with H2O
  3. additionTriethylamine was added dropwise until the solids
  4. dissolutiondissolved
  5. customThe solution was purified by silica gel column chromatography (eluent: 10 to 20% MeOH in CH2Cl2 with 1% NH4OH additive)

出典と根拠

ORDレコード
ord-657daa98f8464f3fb367f9b38ac487e8
出典データセット
uspto-grants-2009_12
特許番号
US07635695B2

反応ノート

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