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Hydrochloric Acid → HCID 178420090, compound

HRID 2407682
Notes
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Reaction equation

HRID 2407682 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([C:30]6[N:34]=[CH:33][N:32](C(C7C=CC=CC=7)(C7C=CC=CC=7)C7C=CC=CC=7)[N:31]=6)[CH:28]=5)[N:23](C5CCCCO5)[N:22]=4)[CH2:15][CH2:14]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.O>[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([CH2:19][NH:20][C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([C:30]6[N:34]=[CH:33][NH:32][N:31]=6)[CH:28]=5)[NH:23][N:22]=4)[CH2:17][CH2:18]3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 58504049HCID 58504049, compound

Product 1

HCID 178420090HCID 178420090, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

The compound prepared in Example 72 (0.13 g) was suspended in a mixture of tetrahydrofuran (6 mL), methanol (6 mL), water (1.5 mL) and concentrated hydrochloric acid (1.5 mL) and heated at reflux overnight. The reaction mixture was cooled to room temperature and poured into a saturated aqueous sodium bicarbonate solution and extracted into ethyl acetate. The organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel to obtain the title compound (0.040 g) having the following physical data.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. extractionextracted into ethyl acetate
  4. dry with materialThe organics were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-420e3f148f8c4f4c9522f5bb1dfbd503
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809538B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes