Methanol → HCID 19104984, compound

HRID 1197792Notes

Reaction equation

HRID 1197792 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]([CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1.CO.Cl.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34]Cl>[OH-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([CH2:34][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=3)([CH2:17][C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 23392Picolyl chloride hydrochlorideHCID 19104983HCID 19104983, compound

Product 1

HCID 19104984HCID 19104984, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 1,3-dihydro-1-(4-chlorophenyl)-3-(4-pyridinylmethyl)-2H-pyrrolo[2,3-b]pyridin-2-one (3.0 g, 8.93 mmol) in 20 ml 1N NaOH was treated with enough MeOH to effect solution. The solution was treated dropwise with a solution of 2-picolylchloride hydrochloride (1.6 g, 9.82 mmol) in 10 ml water over 10 min. The mixture was stirred at room temperature for 16 h, and the resulting solid was colledted by filtration, washed with water, and dried. The solid was recrystallized from CHCl3 --C6H12 to give the desired product in 79% (3.0 g) yield : m.p. 193°-195° ; 1H NMR (300 MHz, CDCl3TMS) δ [3.34 (d, J=12, 1H), 3.56 (d, J=12, 1H) CH2 -(2-Pyr)], [3.48 (d, J=14, 1H), 3.78 (d, J=14, 1H) CH 2 -(4-Pyr)], [6.95 (m, 1H), 8.0 (m, 1H), 8.27 (d, J=7, 1H) Pyr], [7.0 (m, 6H), 7.5 (m, 2H) 2-Pyr & 4-Cl-Phe]), [7.42 (d, J=7, 2H), 8.32 (d, J=7, 2H) 4-Pyr]; IR (Nujol) 1732 (C=O) cm-1 ; MS (NH3 -CI) m/e 427(M+1)/100; Analysis calc'd for C25H19N4OCl H2O: C, 67.49; H, 4.76; N, 12.59; found: C, 67.38; H, 5.01; N, 12.34.

Workup

  1. filtrationthe resulting solid was colledted by filtration
  2. washwashed with water
  3. customdried
  4. customThe solid was recrystallized from CHCl3 --C6H12

Sources & evidence

ORD record
ord-f5cf356bce85459989308db2d33941b8
Source dataset
uspto-grants-1994_01
Patent number
US05278162

Reaction notes

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