Succinic anhydride → HCID 69206585, compound

HRID 586505Notes

Reaction equation

HRID 586505 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:22][C:23]1[C:35](=[O:36])[N:34]([CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:26]2[N:27]=[C:28](S(C)=O)[N:29]=[CH:30][C:25]=2[C:24]=1[CH3:42].C1(=O)OC(=O)CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2[CH:16]=[N:17][C:18]([NH:21][C:28]3[N:29]=[CH:30][C:25]4[C:24]([CH3:42])=[C:23]([Br:22])[C:35](=[O:36])[N:34]([CH:37]5[CH2:38][CH2:39][CH2:40][CH2:41]5)[C:26]=4[N:27]=3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 113721276-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-oneHCID 57440643HCID 57440643, compound

Product 1

HCID 69206585HCID 69206585, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(6-amino-pyridin-3-yl)-azepane-1-carboxylic acid tert-butyl ester (614 mg, 2.10 mmol) in toluene (10 mL) was refluxed in a Dean-Stark apparatus for 3 h. The heat was removed and when the reflux subsided 6-bromo-8-cyclopentyl-2-methanesulfinyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (700 mg, 1.89 mmol) was added. This mixture was refluxed for 12 h under N2. Succinic anhydride (500 mg) was added and the reflux continued for 3 h. The reaction mixture was cooled and dissolved in ethyl acetate (100 ml) and the organic layer was washed with water (100 mL total). The organic layer was dried over magnesium sulfate and the solvents evaporated. The crude product was subjected to chromatography on silica gel and eluted with a chloroform/2-propanol gradient to give 4-[6-(6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-azepane-1-carboxylic acid tert-butyl ester as a yellow powder (414 mg, 0.82 mmol). MS (APCI+) 500, 600 (M+1, 100).

Workup

  1. customThe heat was removed
  2. additionwas added
  3. temperatureThis mixture was refluxed for 12 h under N2
  4. temperatureThe reaction mixture was cooled
  5. washthe organic layer was washed with water (100 mL total)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvents evaporated
  8. washeluted with a chloroform/2-propanol gradient

Sources & evidence

ORD record
ord-e1c085cedf6f438e99fc8fae9abc71d4
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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