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

HRID 1268843Notes

Reaction equation

HRID 1268843 reaction equation
[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

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 18446524HCID 18446524, compound

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-42e31c8bb2f84065b6fc2bcd0965db24
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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