Water → 3-Amino-7-(2-chlorophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carbonitrile

HRID 1455526Notes

Reaction equation

HRID 1455526 reaction equation
Cl[CH2:2][C:3]#[N:4].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]#[N:20])=[C:13]1[S-:21].[Na+].O>CC#N>[NH2:20][C:19]1[C:14]2[CH:15]=[CH:16][C:17](=[O:18])[N:12]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[Cl:5])[C:13]=2[S:21][C:2]=1[C:3]#[N:4]

Participants

5

Reactant 3

HCID 962WaterHCID 7856ChloroacetonitrileHCID 68805809Sodium 1-(2-chlorophenyl)-3-cyano-6-oxo-1,6-dihydropyridine-2-thiolate

Product 1

HCID 669705283-Amino-7-(2-chlorophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carbonitrileYield 33.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

Chloroacetonitrile (0.35 mL, 5.5 mmol) was added to a solution of Example 2 (1.42 g, 5.0 mmol) in MeCN (50 mL) and the mixture heated at 40° C. for 3 h. H2O (100 mL) was added and the mixture concentrated in vacuo to remove some of the MeCN (remaining volume ˜120 mL). The mixture was cooled to 0° C. and the solid filtered off, washed with H2O (15 mL) and Et2O (2×15 mL) and dried to give the title compound as a pale brown solid (505 mg, 32%). δH (DMSO-d6) 8.10 (1H, d, J 9.7 Hz), 7.75-7.73 (1H, m), 7.65-7.54 (3H, m), 7.14 (2H, br s, NH2), 6.54 (1H, d, J 9.7 Hz). LCMS (ES+) RT 2.97 minutes, 302 (M+H)+.

Workup

  1. concentrationthe mixture concentrated in vacuo
  2. customto remove some of the MeCN (remaining volume ˜120 mL)
  3. temperatureThe mixture was cooled to 0° C.
  4. filtrationthe solid filtered off
  5. washwashed with H2O (15 mL) and Et2O (2×15 mL)
  6. customdried

Sources & evidence

ORD record
ord-9e5e167e15994ecb8bf054adb72021fa
Source dataset
uspto-grants-2009_01
Patent number
US07482452B2

Reaction notes

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