Dichloromethane → N-[5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-ylmethyl]-isobutyramide

HRID 1959576Notes

Reaction equation

HRID 1959576 reaction equation
[Cl:1][C:2]1[C:3]([CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:4]([CH2:8][NH2:9])[CH:5]=[N:6][CH:7]=1.C(Cl)Cl.[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>>[Cl:1][C:2]1[C:3]([CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:4]([CH2:8][NH:9][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 62325Isobutyryl chlorideHCID 67077948C-[5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-yl]-methylamine

Product 1

HCID 67077454N-[5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-ylmethyl]-isobutyramide

Procedure

To a solution of C-[5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-yl]-methylamine (0.37 g, 1.4 mmol) in DCM (20 mL) DIPEA (0.41 mL, 2.2 mmol) and isobutyryl chloride (0.18 mL, 1.6 mmol) were added. Stirring was continued overnight at RT. The solvent was evaporated and the residue was used in the following step without further purification. MS (m/z): 326.9 [M+H+].

Workup

  1. customThe solvent was evaporated
  2. customthe residue was used in the following step without further purification

Sources & evidence

ORD record
ord-4b5d426e0bc24c26b47b8a0118b8b7b0
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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