Sodium Bicarbonate → HCID 68458639, compound

HRID 269776Notes

Reaction equation

HRID 269776 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:17][CH2:16]3)=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:26]#[N:27].[Cl:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[S:36][C:37]1[N:38]([CH3:42])[CH:39]=[CH:40][N:41]=1)[NH2:32].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Cl:28][C:29]1[CH:30]=[C:31]([NH:32][C:2]2[C:11]3[C:6](=[CH:7][C:8]([N:15]4[CH2:20][CH2:19][CH:18]([N:21]5[CH2:22][CH2:23][CH2:24][CH2:25]5)[CH2:17][CH2:16]4)=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:26]#[N:27])[CH:33]=[CH:34][C:35]=1[S:36][C:37]1[N:38]([CH3:42])[CH:39]=[CH:40][N:41]=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 68458639HCID 68458639, compoundYield 60.9%

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 95:5methylene 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-yl)quinoline-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 95:5methylene chloride/methanol to 4:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-7f42b46e2a5c405d9a302493f1e13a8d
Source dataset
uspto-grants-2008_11
Patent number
US07449460B2

Reaction notes

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