tert-Butanol → HCID 58840748, compound

HRID 1868297Notes

Reaction equation

HRID 1868297 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-57d9fe39a73c41a29910774e35f5f572
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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