Hydrochloric Acid → HCID 57970192, compound

HRID 1666638Notes

Reaction equation

HRID 1666638 reaction equation
[C:1]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([N:10]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[N:25]=[C:24]([N:26]3[CH2:31][CH2:30][CH2:29][CH:28]([NH:32]C(=O)OCC4C=CC=CC=4)[CH2:27]3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:11]1)=[O:9].Cl>CO.C(OCC)(=O)C.[Pd]>[NH2:32][CH:28]1[CH2:29][CH2:30][CH2:31][N:26]([C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([NH:15][CH:12]3[CH2:13][CH2:14][N:10]([C:8](=[O:9])[CH2:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=4[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH2:11]3)[N:25]=2)[CH2:27]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57970097HCID 57970097, compound

Product 1

HCID 57970192HCID 57970192, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

Benzyl (1-(2-(1-(2-biphenyl-2-ylacetyl)pyrrolidin-3-ylamino)quinazolin-4-yl)piperidin-3-yl)carbamate (570 mg) synthesized in the same manner as the method described in Example 1 was dissolved in methanol (6 mL), followed by addition of a solution (0.25 mL) of 4 M HCl in ethyl acetate and 10% Pd—C (100 mg), and the mixture was stirred at room temperature under hydrogen atmosphere for 3 days. The catalyst was removed by filtration, then the filtrate was concentrated, made basic with saturated aqueous sodium hydrogencarbonate, and then extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate. The desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, then the residue was purified by silica gel column chromatography (chloroform/methanol=3:1), and the resulting compound was solidified in hexane to obtain the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. extractionextracted with chloroform
  4. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  5. customThe desiccant was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform/methanol=3:1)

Sources & evidence

ORD record
ord-285f78c42aef4832966c6b29adc5bb7e
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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