Chloroform → HCID 46869309, compound

HRID 578637Notes

Reaction equation

HRID 578637 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:12][C:13]1[C:22]2[C:17](=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+]=[N-].C(Cl)(Cl)Cl>[Pd].C(O)C>[NH2:1][CH2:4][C@@H:5]([NH:12][C:13]1[C:22]2[C:17](=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 86662382HCID 86662382, compound

Product 1

HCID 46869309HCID 46869309, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-((S)-2-Azido-1-phenyl-ethylamino)-quinazoline-8-carboxylic acid amide ((0.28 g, 0.84 mmol) and palladium on carbon (5%, wet type, 56 mg) were combined in ethanol (5 mL) and chloroform (1 mL) and stirred under an atmosphere of hydrogen for 48 hours. The solution was filtered, rinsed with methanol and the solvent removed under reduced pressure. The sample was redissolved in THF/methanol and hydrogen chloride (4M solution in dioxane, 1 mL) was added. The solid formed was collected by filtration and purified by recrystallization from methanol/ethyl acetate (131 mg, 51%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.27-3.40 (m, 1 H) 3.84-3.98 (m, 1 H) 5.99 (br. s., 1 H) 7.29-7.36 (m, 1 H) 7.39 (t, J=7.39 Hz, 2 H) 7.60 (d, J=7.32 Hz, 2 H) 7.88 (s, 1 H) 8.16 (br. s., 1 H) 8.43 (br. s., 3 H) 8.59 (d, J=0.83 Hz, 1 H) 8.80 (s, 1 H) 9.29 (br. s., 1 H).

Workup

  1. filtrationThe solution was filtered
  2. washrinsed with methanol
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe sample was redissolved in THF/methanol
  5. additionhydrogen chloride (4M solution in dioxane, 1 mL) was added
  6. customThe solid formed
  7. filtrationwas collected by filtration
  8. custompurified by recrystallization from methanol/ethyl acetate (131 mg, 51%)

Sources & evidence

ORD record
ord-42a5af710e6047b5b31d6b65c3e28754
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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