Dimethylamine → HCID 22143566, compound

HRID 985248Notes

Reaction equation

HRID 985248 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) δ8.50 (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-4cb83d178155468fa3d71ef23213d003
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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