Water → HCID 69015439, compound

HRID 1455067Notes

Reaction equation

HRID 1455067 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+].[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36].O>C(#N)C>[CH2:35]([N:37]([CH2:38][CH3:39])[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])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 10046189HCID 10046189, compound

Product 1

HCID 69015439HCID 69015439, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 diethyl amine (63 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. Product was purified by column chromatography using 10% methanol in methylenechloride as eluant. 2-Diethylamino-N-[6-(2-phenyl-chroman-6-yloxy)pyridin-3-yl]acetamide was isolated as its hydrochloride salt. 1H-NMR (400 MHz; d6-DMSO) δ: 11.1 (s, 1H), 8.38 (d, 1H, J 2.7 Hz), 8.04 (dd, 1H, J 2.7, 8.9 Hz), 7.47-7.32 (m, 5H), 7.01 (d, 1H, J 8.9 Hz), 6.89-6.85 (m, 3H), 5.12 (dd, 1H, J 2.0, 10.0 Hz), 4.14 (d, 2H, J 4.9 Hz), 3.24 (k, 4H, J 7.2 Hz), 3.01-2.92 (m, 1H), 2.76-2.70 (m, 1H), 2.19-2.15 (m, 1H), 2.04-1.94 (m, 1H), 1.24 (t, 6H, J 7.2 Hz).

Workup

  1. extractionSolution was extracted with ethyl acetate
  2. extractionOrganic extract
  3. customwas dried
  4. customevaporated
  5. customProduct was purified by column chromatography

Sources & evidence

ORD record
ord-b52c96cfc7b64e0b8906929deb455a3e
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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