Dimethylamine, hydrochloride → HCID 42643631, compound

HRID 1670110Notes

Reaction equation

HRID 1670110 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([C:39]2[CH:43]=[CH:42][S:41][CH:40]=2)[CH:38]=1)[C:33](O)=[O:34])=[O:5])C.C1[CH2:48][N:47]([P+](Br)(N2CCCC2)N2CCCC2)[CH2:46]C1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.CNC.[OH-].[Na+]>C(Cl)Cl.C(OCC)(=O)C.C(O)C.CN(C=O)C>[C:4]([CH2:6][CH2:7][C:8]1[C:9]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:38]=[C:37]([C:39]3[CH:43]=[CH:42][S:41][CH:40]=3)[CH:36]=[C:32]([C:33](=[O:34])[N:47]([CH3:48])[CH3:46])[CH:31]=2)=[CH:10][CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])([OH:3])=[O:5]

Participants

10

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 67338878HCID 67338878, compound

Product 1

HCID 42643631HCID 42643631, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-thiophen-3-yl-benzoic acid (130 mg, 0.21 mmol), PyBroP (263 mg, 0.63 mmol) and diisopropylethylamine (0.11 mL, 0.63 mmol) in CH2Cl2 (4 mL)/DMF (1 mL) was added dimethylamine hydrochloride (51 mg, 0.63 mmol). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The total amount of the product obtained from the previous step was dissolved in ethanol (5 mL) and 1 M NaOH solution was added (2 mL) and the reaction mixture stirred for 3 h. Then the reaction mixture was diluted with ethyl acetate, washed with 10% aq. HCl and brine. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude oil was purified by preparative HPLC using acetonitrile/water gradient to afford the title compound.

Workup

  1. washwashed with brine
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe total amount of the product obtained from the previous step
  6. stirringthe reaction mixture stirred for 3 h
  7. washwashed with 10% aq. HCl and brine
  8. extractionThe organic extract
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe crude oil was purified by preparative HPLC

Sources & evidence

ORD record
ord-510b9f9ea4714c6c8df859116084a978
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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