Hydrochloric Acid → HCID 9953741, compound

HRID 1835100Notes

Reaction equation

HRID 1835100 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:15]2[CH:14]=[CH:13][C:12]3[N:16]=[C:17]([NH:20][C:21]4[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:28])[N:18]([CH3:19])[C:11]=3[C:10]=2[C:9](=[O:29])[NH:8][C:7]=1[CH3:30])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>C1COCC1.O>[Cl:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:28])[C:21]=1[NH:20][C:17]1[N:18]([CH3:19])[C:11]2[C:10]3[C:9](=[O:29])[NH:8][C:7]([CH3:30])=[C:6]([CH2:5][CH2:4][OH:3])[C:15]=3[CH:14]=[CH:13][C:12]=2[N:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 12035491HCID 12035491, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9953741HCID 9953741, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product of Example 9 (25 mg, 0.05 mmol), in THF (2 mL), under nitrogen, was added a solution of lithium aluminum hydride (1M in THF, 0.25 mL, 0.25 mmol). The mixture was stirred for 30min at room temperature. Ethyl acetate was added, followed by water, and then acidified with 1N HCl. The whole mixture was applied to a Varian SCX cartridge, and washed in turn with 1N HCl, water, acetone, MeOH, and MeOH/CH2Cl2 (1:1). The product was then eluted with MeOH/CH2Cl2/NH4OH (49:49:2). Evaporation of the eluent gave the title compound (15 mg, 72%). Mp >300° C.; MS(ES) 417, 419 (MH+).

Workup

  1. washwashed in turn with 1N HCl, water, acetone, MeOH, and MeOH/CH2Cl2 (1:1)
  2. washThe product was then eluted with MeOH/CH2Cl2/NH4OH (49:49:2)
  3. customEvaporation of the eluent

Sources & evidence

ORD record
ord-8b9df7be33194024a90dac612d840e9f
Source dataset
uspto-grants-2004_08
Patent number
US06770639B2

Reaction notes

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