Cyclopentylamine → HCID 69654667, compound

HRID 1826585Notes

Reaction equation

HRID 1826585 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[CH:30]=[CH:29][C:28]([NH2:31])=[N:27][C:25]=4[N:26]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:34]([N:41]1[CH:45]=[CH:44]N=C1)(N1C=CN=C1)=[O:35].[CH:46]1(N)[CH2:50]CC[CH2:47]1>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[CH:30]=[CH:29][C:28]([NH:31][C:34]([NH:41][CH:45]5[CH2:44][CH2:50][CH2:46][CH2:47]5)=[O:35])=[N:27][C:25]=4[N:26]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 2906CyclopentylamineHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 23577086HCID 23577086, compound

Product 1

HCID 69654667HCID 69654667, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.150 g (0.36 mmol) of 4-[4-(7-amino-pyrido[2,3-d]pyrimidin-2-ylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (Example 13) in 2 mL of dimethylformamide, cooled in an ice bath, is added 0.022 g (0.54 mmol) of 60% sodium hydride. The cooled solution is stirred for 15 minutes, then treated with 0.088 g (0.54 mmol) of carbonyldiimidazole. The cooled solution is stirred for another 30 minutes, then treated with 0.071 mL (0.72 mmol) of cyclopentylamine. The resulting solution is stirred at room temperature for 1 hour, then added to cold water. The solid is collected by filtration to give a first crop of material. The aqueous filtrate is then extracted with dichloromethane, and the extracts are dried (magnesium sulfate) and concentrated to give a second crop of material. The 2 crops are combined and purified by flash chromatography, eluting with a gradient of 0% to 5% methanol/dichloromethane during 30 minutes to give 0.1159 g (60.4%) of the product as a solid.

Workup

  1. stirringThe cooled solution is stirred for another 30 minutes
  2. stirringThe resulting solution is stirred at room temperature for 1 hour
  3. filtrationThe solid is collected by filtration
  4. customto give a first crop of material
  5. extractionThe aqueous filtrate is then extracted with dichloromethane
  6. dry with materialthe extracts are dried (magnesium sulfate)
  7. concentrationconcentrated
  8. customto give a second crop of material
  9. custompurified by flash chromatography
  10. washeluting with a gradient of 0% to 5% methanol/dichloromethane during 30 minutes

Sources & evidence

ORD record
ord-578edd1f7b9f43e7a8e9feaf3ca382d7
Source dataset
uspto-grants-2006_05
Patent number
US07053070B2

Reaction notes

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