Hydrochloric Acid → HCID 11283587, compound

HRID 2054600Notes

Reaction equation

HRID 2054600 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:40])[CH2:6][CH2:7][C:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=2)[N:12]([CH2:20][C:21]2[CH:22]=[N:23][C:24]([C:27]3[C:32]4[O:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[C:31]=4[CH:30]=[CH:29][CH:28]=3)=[CH:25][CH:26]=2)[CH:11]=1)=[O:9].Cl>O1CCCC1.CO.O>[Cl:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:20][C:21]1[CH:22]=[N:23][C:24]([C:27]3[C:32]4[O:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[C:31]=4[CH:30]=[CH:29][CH:28]=3)=[CH:25][CH:26]=1)[CH:11]=[C:10]2[C:8](=[O:9])[CH2:7][CH2:6][C:5]([OH:40])=[O:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69299386HCID 69299386, compound

Product 1

HCID 11283587HCID 11283587, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2N Sodium hydroxide solution (1.45 mL, 2.9 mmol) was added dropwise to a stirred solution of methyl-4-[5-chloro-1-(6-dibenzofuran-4-yl-pyridin-3-ylmethyl)-1H-indol-3-yl]-4-oxo-butyrate (500 mg, 0.95 mmol) in tetrahydrofuran (10 mL) and methanol (2 mL). The clear reaction mixture was stirred at room temperature until the reaction was complete (TLC control), and then diluted with water (10 mL), and acidified to pH 3 with 2N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (2×20 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 5% methanol in methylene chloride as eluent, afforded the title compound as a white solid (475 mg, 98%): Rf: 0.35 (10% methanol in dichloromethane); 1H NMR (DMSO-d6, 300 MHz) δ 8.82 (1H, d, J=2 Hz, ArH), 8.76 (1H, s, ArH), 8.31 (1H, d, J=8 Hz, ArH), 8.18 (4H, m, ArH), 7.88 (1H, dd, J=8, 2 Hz, ArH), 7.72 (2H, d, J=9 Hz, ArH), 7.50 (2H, q, J=6 Hz, ArH), 7.40 (1H, t, J=7 Hz, ArH), 7.27 (1H, dd, J=8, 2 Hz, ArH), 5.65 (2H, s, CH2N), 3.16 (2H, t, J=7 Hz, CH2CO), 2.59 (2H, t, J=7 Hz, CH2CO); ESI-LCMS e/z calculated for C30H21ClN2O4 508.950, found 509 [M+H (35Cl)]+, 511 [M+H (37Cl)]+, 531 [M+Na (35Cl)]+, 533 [M+Na (37Cl)]+.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×20 mL)
  2. extractionThe combined extract
  3. washwas washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the product by flash column chromatography

Sources & evidence

ORD record
ord-4398dee5622d4d1db508e173ea74c62d
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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