Potassium Carbonate → HCID 66757985, compound

HRID 242687Notes

Reaction equation

HRID 242687 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][N:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29]/[CH:30]=[C:31]1/[C:32]2[CH:45]=[C:44]([C:46]([OH:49])([CH3:48])[CH3:47])[CH:43]=[CH:42][C:33]=2[O:34][CH2:35][C:36]2[N:41]=[CH:40][CH:39]=[CH:38][C:37]/1=2>C(#N)C.O>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][N:6]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)[CH:7]1[CH2:11][CH2:10][N:9]([CH2:28][CH2:29][CH:30]=[C:31]2[C:37]3[CH:38]=[CH:39][CH:40]=[N:41][C:36]=3[CH2:35][O:34][C:33]3[CH:42]=[CH:43][C:44]([C:46]([OH:49])([CH3:48])[CH3:47])=[CH:45][C:32]2=3)[CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23136844(E)-2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-olHCID 66758252HCID 66758252, compound

Product 1

HCID 66757985HCID 66757985, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-[(4-chloro-benzyl)-pyrrolidin-3-yl-amino]-propionic acid methyl ester (0.06 g, 0.2 mmol) in acetonitrile:water (3:1) was added potassium carbonate (0.056 g, 0.4 mmol) and (E)-2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.065 g, 0.17 mmol) and reaction stirred at 50° C. for 24 h. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and dried over sodium sulfate. The crude product was purified by flash chromatography on silica using ethyl acetate/methanol (5%). 1H-NMR (CDCl3) δ: 1.40 (6H, s), 1.60 (1H, m), 1.80 (1H, m), 2.10-2.60 (8H, m), 3.20-3.40 (6H, m), 3.50 (2H, m; 2H, s), 5.20 (2H, br s), 6.15 (1H, t), 6.70 (1H, t), 7.18-7.42 (7H, m), 7.70 (1H, dd), 8.50 (1H, dd). ESI-MS m/z: 590 (M+1), UV retention time: 1.51 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-d1f04c5a6f374fabb1343147a3dbed1d
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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