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Sodium Iodide → Ethyl 2-[4-({[(6-amino-5-chloro-2-methoxypyridin-3-yl)carbonyl]amino}methyl)piperidin-1-yl]hexanoate

HRID 489808
Notes
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Reaction equation

HRID 489808 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1[Cl:20].Br[CH:22]([CH2:28][CH2:29][CH2:30][CH3:31])[C:23]([O:25][CH2:26][CH3:27])=[O:24].[I-].[Na+].C(N(CC)CC)C>CN(C)C=O.O>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH:22]([CH2:28][CH2:29][CH2:30][CH3:31])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1[Cl:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 79072Ethyl 2-bromohexanoateHCID 222625966-amino-5-chloro-2-(methyloxy)-N-(4-piperidinylmethyl)-3-pyridinecarboxamide

Product 1

HCID 22262611Ethyl 2-[4-({[(6-amino-5-chloro-2-methoxypyridin-3-yl)carbonyl]amino}methyl)piperidin-1-yl]hexanoateYield 94.2%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-amino-5-chloro-2-(methyloxy)-N-(4-piperidinylmethyl)-3-pyridinecarboxamide (step 1 in example 13, 4.0 g, 13 mmol) in dimethylformamide (70 ml) was added ethyl 2-bromohexanoate (3.1 g, 14 mmol), sodium iodide (2.0 g, 13 mmol) and triethyl amine (2.2 ml) at room temperature. The mixture was heated at 70° C. overnight. After cooled to room temperature, the mixture was poured into water (80 ml) and extracted with diethyl ether (200 ml×2), washed with water (100 ml×2), brine (100 ml). The organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1) to give 5.4 g (93%) of the title compound as a clear colorless solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with diethyl ether (200 ml×2)
  3. washwashed with water (100 ml×2), brine (100 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-653396161e6b4cf68f4f02f671223bfa
Source dataset
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06979690B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes