Dimethylformamide → HCID 69768834, compound

HRID 2415384Notes

Reaction equation

HRID 2415384 reaction equation
Cl.O1C2C=CC([C@@H:11]3[C:15]4[NH:16][C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=5[C:23](=[O:24])[C:14]=4[CH2:13][NH:12]3)=CC=2CC1.Cl[C:26]1[N:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:28][N:27]=1.[F-].[K+].C(N([CH:46]([CH3:48])[CH3:47])CC)(C)C.CN([CH:52]=[O:53])C>CO.ClCCl.CCOC(C)=O>[N:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C:29]1[CH:28]=[N:27][C:26]([N:12]2[CH2:13][C:14]3[C:23](=[O:24])[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[NH:16][C:15]=3[C@@H:11]2[CH:11]2[CH2:15][CH:14]3[CH2:13][CH:48]=[CH:46][CH:47]=[C:52]3[O:53]2)=[N:31][CH:30]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 167263772-Chloro-5-(pyridin-2-yl)pyrimidineHCID 69479994HCID 69479994, compound

Product 1

HCID 69768834HCID 69768834, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of (R)-1,2,3,4-Tetrahydro-3-(2,3-dihydrobenzofuran-5-yl)-9H-pyrrolo-[3,4-b]quinolin-9-one, hydrochloride salt (1.273 g, 0.00373 mole) (prepared in example 6A), 2-chloro-5-(2-pyridinyl)pyrimidine (0.714 g, 0.00373 mole), KF (0.216 g, 0.00373 mole), and diisopropylethylamine (2.27 mL) in DMF (45 mL) was heated at 55° C. for 4 h. EtOAc was added, and the mixture was washed with 0.5N citric acid, then with 15% NaCl, brine and dried over MgSO4. Solvent was distilled out under reduced pressure to give a solid. The solid was dissolved in 10% methanol in dichloromethane and purified via column chromatography (EtOAc to 10% CH3OH in EtOAc) to yield the title compound.

Workup

  1. washthe mixture was washed with 0.5N citric acid
  2. dry with materialwith 15% NaCl, brine and dried over MgSO4
  3. distillationSolvent was distilled out under reduced pressure
  4. customto give a solid
  5. custompurified via column chromatography (EtOAc to 10% CH3OH in EtOAc)

Sources & evidence

ORD record
ord-d7fa101b54bb4b3fa33ce577eecf26c0
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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