Sulfuric Acid → 4-Amino-2-imidazol-1-yl-thieno[3,2-c]pyridine-7-carboxylic acid amide

HRID 1268848Notes

Reaction equation

HRID 1268848 reaction equation
[N:1]1([C:6]2[S:14][C:13]3[C:12]([C:15]#[N:16])=[CH:11][N:10]=[C:9]([NH:17]CC4C=CC(OC)=CC=4)[C:8]=3[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH:27]S(O)(=O)=O>>[NH2:17][C:9]1[C:8]2[CH:7]=[C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[S:14][C:13]=2[C:12]([C:15]([NH2:16])=[O:27])=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 184465232-Imidazol-1-yl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile

Product 1

HCID 588407444-Amino-2-imidazol-1-yl-thieno[3,2-c]pyridine-7-carboxylic acid amide

Procedure

To 2-imidazol-1-yl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile 37 (0.050 g, 0.14 mmol) was added H2SO4 (0.25 mL). After stirring at room temperature for 1 h, 2 g of ice were added to the solution. The precipitate was filtered, washed with H2O, then dissolved in 30% methanol, 2.5% triethylamine in CH2Cl2. The solution was concentrated, the solid was suspended in H2O, then filtered and rinsed with H2O resulting in pure 38. 1H NMR (400 MHz, d6-DMSO) δ 8.57 (s, 1H), 8.17 (s, 1H), 8.02 (bs, 1H), 7.77 (s, 1H), 7.67 (bs, 1H), 7.39 (bs, 1H), 7.18 (m, 3H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with H2O
  3. dissolutiondissolved in 30% methanol
  4. concentrationThe solution was concentrated
  5. filtrationfiltered
  6. washrinsed with H2O resulting in pure 38

Sources & evidence

ORD record
ord-2709c0e56be6499697bad45c59f2edcb
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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