HCID 11188518, compound → HCID 11215611, compound

HRID 1271927Notes

Reaction equation

HRID 1271927 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][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)([CH3:4])([CH3:3])[CH3:2].[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:42]=[N:43][C:44]([NH2:47])=[CH:45][CH:46]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C1(C)C=CC=CC=1>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:42]=[N:43][C:44]([NH:47][C:13]3[N:14]=[CH:15][C:10]4[CH:9]=[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:27])[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:45][CH:46]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 11188518HCID 11188518, compoundHCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 11215611HCID 11215611, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
105 °C

Procedure

(8-Cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-carbamic acid tert-butyl ester (1.2 g, 3.06 ml, prepared according to Example 9) and 4-(6-amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (2.36 g, 8.48 mmol) were combined in toluene (4 ml) and heated to 105° C. for 12 hours. The resulting paste was diluted with toluene, filtered, washed with toluene and partitioned between diethyl ether and 1 N citric acid. The mixture was filtered, and the solid was washed with water and diethyl ether. The solid then was dissolved in chloroform, dried over anhydrous magnesium sulfate, filtered, and the filtrate diluted with diethyl ether, giving a solid precipitate. This solid was collected by filtration and dried in vacuo to give 4-[6-(6-tert-butoxycarbonylamino-8-cyclopentyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester as a solid (0.311 g, 17%). MS (APCI) M++1; Calc'd, 607.3, Found, 607.2.

Workup

  1. filtrationfiltered
  2. washwashed with toluene
  3. custompartitioned between diethyl ether and 1 N citric acid
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with water and diethyl ether
  6. dissolutionThe solid then was dissolved in chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. additionthe filtrate diluted with diethyl ether
  10. customgiving a solid precipitate
  11. filtrationThis solid was collected by filtration
  12. customdried in vacuo

Sources & evidence

ORD record
ord-29db0c6d7e0c4dfb93adf21b458aa6b8
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

Loading…