2,6-Dichlorpyridine-3-carbonyl chloride → HCID 178523747, compound

HRID 2042815Notes

Reaction equation

HRID 2042815 reaction equation
[F:1][C:2]([F:11])([F:10])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH2:9])[CH2:5][CH2:4]1.[Cl:12][C:13]1[N:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>C1COCC1>[Cl:12][C:13]1[N:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15]([NH:9][C@H:6]1[CH2:5][CH2:4][C@H:3]([C:2]([F:10])([F:11])[F:1])[CH2:8][CH2:7]1)=[O:16]

Participants

4

Reactant 2

HCID 122639842,6-Dichlorpyridine-3-carbonyl chlorideHCID 178511531HCID 178511531, compound

Product 1

HCID 178523747HCID 178523747, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of trans-4-trifluoromethyl-cyclohexylamine (4.8 g) and TEA (8.3 mL, 59.4 mmol) in THF (150 mL) is stirred for 20 min at rt. 2,6-Dichloro-nicotinoyl chloride (5.0 g, 23.8 mmol) in THF (50 mL) is added dropwise under cooling and the mixture is stirred at rt for 2 h. The reaction mixture is filtered and the filtrate is concentrated. The residue is treated with water, filtered off, washed with water and dried to give the sub-title compound.

Workup

  1. temperatureunder cooling
  2. stirringthe mixture is stirred at rt for 2 h
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. additionThe residue is treated with water
  6. filtrationfiltered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-af8fe419a81d4fc5b6447586c57eb546
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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