Sodium Bicarbonate → HCID 86628426, compound

HRID 499123Notes

Reaction equation

HRID 499123 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8](N3CCC(N4CCCC4)CC3)=[C:9]([N+]([O-])=O)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:26]#[N:27].ClC1C=[C:31]([CH:33]=[CH:34][C:35]=1SC1N(C)C=CN=1)[NH2:32].Cl.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[N:32]1([CH:47]2[CH2:48][CH2:49][N:44]([C:4]3[C:3]([C:26]#[N:27])=[CH:2][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH2:45][CH2:46]2)[CH2:31][CH2:33][CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 114590883-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamineHCID 68460168HCID 68460168, compound

Product 1

HCID 86628426HCID 86628426, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 0.5 g (1.45 mmol) of 4-chloro-6-nitro-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile, 0.38 g (1.6 mmol) of 3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]aniline and 0.17 g of pyridine hydrochloride in 7.0 mL of 2-ethoxyethanol is heated at 105° C. for 1 hour. After cooling to room temperature, the mixture is stirred with 15 mL of saturated solution of sodium bicarbonate. The resulting solid is collected by filtration and washed with water. Some of the product dissolves in water, which is recovered by extracting the aqueous layer with solution of 95:5 methylene chloride/methanol. The organic layer is evaporated to provide crude product. The combined solids are purified by silica gel chromatography (gradient 95:5 methylene chloride/methanol to 4:1 methylene chloride/methanol) gives 0.52 g of 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-6-nitro-7-(4-pyrrolidin-1-ylpiperidin-1-ylquinoline-3-carbonitrile as an orange solid, mp 220-230° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with water
  4. dissolutionSome of the product dissolves in water
  5. customwhich is recovered
  6. extractionby extracting the aqueous layer with solution of 95:5 methylene chloride/methanol
  7. customThe organic layer is evaporated
  8. customto provide crude product
  9. customThe combined solids are purified by silica gel chromatography (gradient 95:5 methylene chloride/methanol to 4:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-b4867b1eba5542deb2bfcec31bb33e82
Source dataset
uspto-grants-2010_08
Patent number
US07767671B2

Reaction notes

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