Hydrochloric Acid → HCID 20634944, compound

HRID 460382Notes

Reaction equation

HRID 460382 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:15]2[CH:16]=[CH:17][C:18]([N:21]3[CH2:27][CH2:26][CH2:25][N:24]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[C:38]([C:40](OC)=[O:41])[CH:37]=[C:36]([C:44](OC)=[O:45])[CH:35]=5)=[CH:30][N:29]=4)[CH2:23][CH2:22]3)=[N:19][CH:20]=2)[CH:8]=[C:9]([C:11](OC)=[O:12])[CH:10]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.CO.Cl.[OH-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[OH:41][CH2:40][C:38]1[CH:39]=[C:34]([C:31]2[CH:32]=[CH:33][C:28]([N:24]3[CH2:25][CH2:26][CH2:27][N:21]([C:18]4[CH:17]=[CH:16][C:15]([C:7]5[CH:6]=[C:5]([CH2:3][OH:2])[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=5)=[CH:20][N:19]=4)[CH2:22][CH2:23]3)=[N:29][CH:30]=2)[CH:35]=[C:36]([CH2:44][OH:45])[CH:37]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1140TolueneHCID 14798Sodium HydroxideHCID 20634945HCID 20634945, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20634944HCID 20634944, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-20 °C

Procedure

Under nitrogen, a solution of 1,4-bis[5-[3,5-bis(methoxycarbonyl)phenyl]-2-pyridyl]hexahydro-1,4-diazepine (17.0 mg, 0.0266 mmol), which had been synthesized in Example 20, in anhydrous tetrahydrofuran (1.0 mL) was cooled to −20° C. To the resulting solution was added a 1.0 M solution of diisobutylaluminum hydride in toluene (0.40 mL, 0.40 mmol), and the resulting mixture was stirred for 1 hour. Methanol (0.2 mL, 4.9 mmol) was added to the mixture, and the bath was removed, then 0.50 M hydrochloric acid (1.0 mL, 0.50 mmol) was added. The mixture was stirred at room temperature for 1 hour, and a 1.0 M aqueous sodium hydroxide (1.0 mL, 1.0 mmol) and brine were added. The resulting mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative thin-layer chromatography on silica gel to yield the title compound as a colorless amorphous powder (7.4 mg, yield: 53%).

Workup

  1. customthe bath was removed
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. extractionThe resulting mixture was extracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative thin-layer chromatography on silica gel

Sources & evidence

ORD record
ord-b81bd470ae3d4532b0668c05fa90e3e9
Source dataset
uspto-grants-2007_03
Patent number
US07196101B2

Reaction notes

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