tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate → HCID 69206658, compound

HRID 272434Notes

Reaction equation

HRID 272434 reaction equation
[CH2:1]([C:8]1[C:20](=[O:21])[N:19]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[C:11]2[N:12]=[C:13](S(C)=O)[N:14]=[CH:15][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:41]=[N:42][C:43]([NH2:46])=[CH:44][CH:45]=2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>C1(C)C=CC=CC=1>[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:41]=[N:42][C:43]([NH:46][C:13]3[N:14]=[CH:15][C:10]4[CH:9]=[C:8]([CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[C:20](=[O:21])[N:19]([CH:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[C:11]=4[N:12]=3)=[CH:44][CH:45]=2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylateHCID 22329912HCID 22329912, compound

Product 1

HCID 69206658HCID 69206658, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Benzyl-8-cyclopentyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.64 g, 1.74 mmol) and 4-(6-Amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.87 g, 2.96 mmol) in toluene (10 ml) were heated to 95° C. for 28 hours. The reaction mixture was allowed to cool then chromatographed on silica gel using a gradient of 20 to 50% ethyl acetate in hexane. The product-containing fractions were evaporated and the residue was triturated with acetonitrile to give a solid. This solid was collected by filtration and dried in vacuo to provide 4-[6-(6-benzyl-8-cyclopentyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.201 g, 19.8%). MS (APCI) M++1: Calc'd, 582.31. Found, 582.3.

Workup

  1. temperatureto cool
  2. customthen chromatographed on silica gel using a gradient of 20 to 50% ethyl acetate in hexane
  3. customThe product-containing fractions were evaporated
  4. customthe residue was triturated with acetonitrile
  5. customto give a solid
  6. filtrationThis solid was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b7c2e77c0dae46c2b763864bca66d044
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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