Dimethylamine → HCID 22143566, compound

HRID 1825127Notes

Reaction equation

HRID 1825127 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:16]=[C:15]([CH:17]=O)[CH:14]=[CH:13][CH:12]=3)[S:10][C:3]=12.[CH3:19][NH:20][CH3:21].[BH3-]C#N.[Na+].CC([O-])=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:16]=[C:15]([CH2:17][N:20]([CH3:21])[CH3:19])[CH:14]=[CH:13][CH:12]=3)[S:10][C:3]=12

Participants

6

Reactant 4

HCID 674DimethylamineHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 22143597HCID 22143597, compound

Product 1

HCID 22143566HCID 22143566, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-(7-chlorothieno[3,2-b]pyridin-2-yl)pyridine-2-carbaldehyde 52a (0.127 g, 0.46 mmole) in THF (20 ml) was added 2.0 M dimethylamine in THF (1.5 ml, 2.3 mmole), NaCNBH3 (0.063 g, 0.92 mmole) and NaOAc (0.076 g, 0.92 mmole). The reaction mixture was stirred at room temperature overnight and concentrated. The residue was purified by flash column chromatography eluting with 2–10% CH3OH in CHCl3 to give a yellow solid (0.086 g, 61%). 1H NMR (300 MHz, CD3OD) δ 8.50 (1H, d, J=5.3 Hz), 8.11 (1H, s), 8.03 (1H, d, J=7.9 Hz), 7.90 (1H, t, J=7.9 Hz), 7.41 (2H, m), 4.16 (2H, s), 2.71 (6H, s).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography
  3. washeluting with 2–10% CH3OH in CHCl3

Sources & evidence

ORD record
ord-f68cc023eafa4c1ab2493d7bf370fa45
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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