2-Chloro-6-fluorobenzoyl chloride → HCID 66938907, compound

HRID 1716939Notes

Reaction equation

HRID 1716939 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[N:4]=1.[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:19]=1[C:20](Cl)=[O:21]>O1CCOCC1>[ClH:17].[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:19]=1[C:20]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:1])[CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[N:4]=1)=[O:21]

Participants

4

Reactant 2

HCID 27365472-Chloro-6-fluorobenzoyl chlorideHCID 58997271N-methyl N-(1-methyl-piperidin-4-yl)-pyridine-2,6-diamine

Product 1

HCID 66938907HCID 66938907, compoundYield 150.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Prepare according to procedure in Example 66 starting with N-methyl-N-(1-methyl-piperidin-4-yl)-pyridine-2,6-diamine (Preparation 34) (200 mg, 0.907 mmol), 2-chloro-6-fluorobenzoyl chloride (179 mg, 0.998 mmol), and 1,4-dioxane (10 mL) to yield 310 mg (83%) of the title compound: mass spectrum (ion spray): m/z=377.2 (M+1); Analysis calc'd for C19H23N4OCl2.0.5H2O: C, 54.03; H, 5.73; N, 13.27. Found: C, 53.71; H, 5.71; N, 13.45. mp 283-6° C.

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-fef11b6902c1443e8b9014c221e2270e
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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