tert-Butanol → HCID 58840748, compound

HRID 1268844Notes

Reaction equation

HRID 1268844 reaction equation
[C:1]1([C:6]2[S:14][C:13]3[C:12]([C:15]#[N:16])=[CH:11][N:10]=[C:9]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:8]=3[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.[OH-].[K+].C([OH:33])(C)(C)C>C(Cl)Cl>[C:1]1([C:6]2[S:14][C:13]3[C:12]([C:15]([NH2:16])=[O:33])=[CH:11][N:10]=[C:9]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:8]=3[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 18446521HCID 18446521, compound

Product 1

HCID 58840748HCID 58840748, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Cyclopent-1-enyl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile 32 (0.020 g, 0.055 mmol), crushed KOH (0.10 g) and tert-butanol (1.5 mL) was brought to reflux for 45 minutes. The reaction mixture was diluted with CH2Cl2 (20 mL) and extracted with H2O (5 mL). The organic layer was concentrated in vacuo to provide 33. 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 7.34 (d, J=8 Hz, 2H), 6.91 (m, 3H), 6.24 (m 1H), 5.93 (bs, 2H), 5.37 (t, J=5 Hz,1H), 4.78 (d, J=5 Hz, 2H), 3.83 (s, 3H), 2.73 (m, 2H), 2.57 (m, 2H), 2.04 (p, J=7 Hz, 2H).

Workup

  1. temperatureto reflux for 45 minutes
  2. extractionextracted with H2O (5 mL)
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-0e5ffff429a54b08b291345e95e76a81
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

Loading…