Sodium borohydride → HCID 58840722, compound

HRID 1268869Notes

Reaction equation

HRID 1268869 reaction equation
[NH2:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:20]=[CH:19][C:18]4[CH2:17][C:16](=[O:21])[CH2:15][CH2:14][C:13]=4[CH:12]=3)[S:10][C:6]=2[C:5]([C:22]([NH2:24])=[O:23])=[CH:4][N:3]=1.[BH4-].[Na+]>C(O)C>[NH2:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:20]=[CH:19][C:18]4[CH2:17][CH:16]([OH:21])[CH2:15][CH2:14][C:13]=4[CH:12]=3)[S:10][C:6]=2[C:5]([C:22]([NH2:24])=[O:23])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23585502HCID 23585502, compound

Product 1

HCID 58840722HCID 58840722, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-amino-2-(6-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-thieno[3,2-c]pyridine-7-carboxylic acid amide 89 (24.5 mg, 0.07 mmol) in absolute ethanol (4 mL) was added sodium borohydride (11.5 mg, 0.30 mmol). After 1.25 h at room temperature, the reaction mixture was concentrated, partially dissolved in a mixture of DMSO and MeOH, and filtered. The filtrate was purified by reverse phase preparative HPLC to give 90. 1H NMR (400 MHz, d6-DMSO) δ: 1.63–1.74 (m, 1H), 1.87–1.96 (m, 1H), 2.57–2.68 (m, 1H), 2.73–2.81 (m, 1H), 2.90–3.02 (m, 2H), 3.93–4.01 (m, 2H), 7.20 (d, J=8.0 Hz, 1H), 7.44–7.48 (m, 2H), 7.70–7.83 (br s, 1H), 8.26 (s, 2H), 8.41 (s, 1H), 8.63–8.83 (br s, 2H). MS (EI) m/z (M+H+) 340, (2M+H+) 679.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionpartially dissolved in a mixture of DMSO and MeOH
  3. filtrationfiltered
  4. customThe filtrate was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-837eaad0c78b4bda9e482cf37f7e8175
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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