Water → HCID 69016536, compound

HRID 1455064Notes

Reaction equation

HRID 1455064 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+].[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.O>C(#N)C>[C:23]1([CH:18]2[CH2:17][CH2:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([O:12][C:9]4[N:8]=[CH:7][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)=[CH:11][CH:10]=4)[CH:14]=3)[O:19]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 10046189HCID 10046189, compound

Product 1

HCID 69016536HCID 69016536, 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 pyrrolidine (51 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. N-[6-(2-Phenyl-chroman-6-yloxy) pyridin-3-yl]-2-pyrrolidin-1-yl acetamide was isolated as its hydrochloride salt. 1H-NMR (400 MHz; d6-DMSO) δ: 10.8 (s, 1H), 8.35 (d, 1H, J 2.7 Hz), 8.02 (dd, 1H, J 2.7, 8.9 Hz), 7.47-7.32 (m, 5H), 7.00 (d, 1H, J 8.9 Hz), 6.89-6.85 (m, 3H), 5.12 (dd, 1H, J 1.9, 10.0 Hz), 4.25 (d, 2H, 5.4 Hz), 3.67-3.55 (m, 2H), 3.20-3.06 (m, 2H), 3.06-2.90 (m, 1H), 2.80-2.65 (m, 1H), 2.23-2.12 (m, 1H), 2.10-1.85 (m, 5H).

Workup

  1. extractionSolution was extracted with ethyl acetate
  2. extractionOrganic extract
  3. customwas dried
  4. customevaporated

Sources & evidence

ORD record
ord-c25677fcb6934709b4d6e1173ae30f82
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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