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Water → HCID 69016920, compound

HRID 1455065
Notes
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Reaction equation

HRID 1455065 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][CH:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][CH2:16]3)=[CH:10][CH:11]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:35][CH:36]1[CH2:40][CH2:39][CH:38]([CH3:41])[NH:37]1.O>C(#N)C>[CH3:35][CH:36]1[CH2:40][CH2:39][CH:38]([CH3:41])[N:37]1[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][CH:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][CH2:16]3)=[CH:10][CH:11]=1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 960342,5-DimethylpyrrolidineHCID 10046189HCID 10046189, compound

Product 1

HCID 69016920HCID 69016920, compound

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

Procedure

To a solution of 2-Chloro-N-[6-(2-phenylchroman-6-yloxy)-pyridin-3-yl]-acetamide (200 mg) in acetonitrile was added potassium carbonate (133 mg) and 2,5-dimethylpyrrolidine (81 μl). The mixture was stirred at room temperature. Water was added to the reaction mixture. Solution was extracted with ethyl acetate. Organic extract was dried and evaporated. The product was purified by column chromatography using gradient elution with methanol-dichloromethane (2%->5%). 1H-NMR (300 MHz; d6-DMSO) δ: 9.66 (s, 1H), 8.35 (d, 1H, J 2.7 Hz), 8.06 (dd, 1H, J 2.7, 8.8 Hz), 7.47-7.32 (m, 5H), 6.93 (d, 1H, J 8.8 Hz), 6.88-6.84 (m, 3H), 5.12 (dd, 1H, J 2.1, 9.9 Hz), 3.22 (s, 2H), 3.05-2.88 (m, 1H), 2.78-2.66 (m, 3H), 2.22-2.12 (m, 1H), 2.08-1.92 (m, 1H), 1.90-1.79 (m, 2H), 1.43-1.34 (m, 2H), 1.06 (d, 6H, J 6.1 Hz).

Workup

  1. extractionSolution was extracted with ethyl acetate
  2. extractionOrganic extract
  3. customwas dried
  4. customevaporated
  5. customThe product was purified by column chromatography
  6. washelution with methanol-dichloromethane (2%->5%)

Sources & evidence

ORD record
ord-dc4cfe83e5e84abb877352dbb7a42d1b
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07482340B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes