4-(1-Pyrrolidinyl)piperidine → HCID 58046361, compound

HRID 1035797Notes

Reaction equation

HRID 1035797 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[N:24]([S:27]([C:30]5[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=5)(=[O:29])=[O:28])[CH:25]=[CH:26][C:19]=34)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[N:37]1([CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH2:41][CH2:40][CH2:39][CH2:38]1>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([N:45]4[CH2:46][CH2:47][CH:42]([N:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[CH2:43][CH2:44]4)=[N:7][N:6]3[C:8]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[N:24]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[CH:25]=[CH:26][C:19]=23)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 58046364HCID 58046364, compound

Product 1

HCID 58046361HCID 58046361, compoundYield 78.1%

Conditions

Temperature
140 °C

Procedure

A mixture of 0.15 g (0.29 mmol) of 6-chloro-2-(4-fluorophenyl)-3-[1-(4-methylphenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazine, prepared according to the method described in step 3.2 of Example 3, and 0.179 g (1.16 mmol) of 4-pyrrolidin-1-ylpiperidine is heated under reflux for 40 hours at 140° C. The reaction medium is cooled. The crystalline solid which forms on cooling is triturated in 1 ml of diisopropyl ether and is isolated by centrifugation and removal of the supernatant in order to give 0.144 g of 2-(4-fluorophenyl)-6-(4-pyrrolidin-1-ylpiperidin-1-yl)-3-[1-(4-methylphenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazine, used without additional purification in the remainder of the synthesis.

Workup

  1. customprepared
  2. temperatureis heated
  3. temperatureThe reaction medium is cooled
  4. temperatureThe crystalline solid which forms on cooling
  5. customis triturated in 1 ml of diisopropyl ether
  6. customis isolated by centrifugation and removal of the supernatant in order

Sources & evidence

ORD record
ord-bdeef68ff6b04255ae689fc276d787b3
Source dataset
uspto-grants-2013_10
Patent number
US08546395B2

Reaction notes

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