HCID 131715224, compound → HCID 53665640, compound

HRID 2118958Notes

Reaction equation

HRID 2118958 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][CH:10]([C:16]1[CH:17]=[C:18]([CH:47]=[CH:48][CH:49]=1)[O:19][C@@H:20]1[CH2:24][N:23]([C:25]([N:27]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH3:29])=[O:26])[C@H:22]([C:37]([O:39]CC3C=CC=CC=3)=[O:38])[CH2:21]1)[NH:9][C:8]2=[O:50])(=[O:4])=[O:3]>[Pd].C(O)C>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][CH:10]([C:16]1[CH:17]=[C:18]([CH:47]=[CH:48][CH:49]=1)[O:19][C@@H:20]1[CH2:24][N:23]([C:25]([N:27]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH3:29])=[O:26])[C@H:22]([C:37]([OH:39])=[O:38])[CH2:21]1)[NH:9][C:8]2=[O:50])(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 131715224HCID 131715224, compound

Product 1

HCID 53665640HCID 53665640, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the phenylmethyl ester product of part (i) (505 mg., 0.69 mmole) in 40 ml. of absolute ethanol is added approximately 70 mg. of 10% palladium on charcoal. The resulting mixture is stirred under hydrogen for approximately 2.5 hours at which time Tlc analysis shows no starting material remaining. The mixture is filtered and concentrated at reduced pressure to give a pale gray foam which is dried under vacuum overnight to give 430 mg. of material. In order to remove additional palladium/charcoal, this material is dissolved in ethanol, millipore filtered, and concentrated at reduced pressure. The residue is dissolved in tetrahydrofuran, precipitated with ether to give a white solid, and dried overnight under vacuum to give (cis)-4-[3-[6-(aminosulfonyl)-7-chloro-1,2,3,4-tetrahydro-4-oxo-2-quinazolinyl]phenoxy]-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-L-proline.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated at reduced pressure
  3. customto give a pale gray foam which
  4. customis dried under vacuum overnight
  5. customto give 430 mg
  6. customIn order to remove additional palladium/charcoal
  7. dissolutionthis material is dissolved in ethanol
  8. filtrationmillipore filtered
  9. concentrationconcentrated at reduced pressure
  10. dissolutionThe residue is dissolved in tetrahydrofuran
  11. customprecipitated with ether
  12. customto give a white solid
  13. customdried overnight under vacuum

Sources & evidence

ORD record
ord-17be5510112a4e0db70cc37a5398bf75
Source dataset
uspto-grants-1987_07
Patent number
US04681886

Reaction notes

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