D-Proline → HCID 25145804, compound

HRID 1257798Notes

Reaction equation

HRID 1257798 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([S:11][CH2:12][CH:13]=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1CCC[C@@H]1C(O)=O.ClN1C(=O)CCC1=O.[NH2:31][C:32]1[N:33]=[N:34][C:35]([C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[C:40]([F:48])[CH:39]=2)=[CH:36][N:37]=1>C(Cl)(Cl)Cl>[F:48][C:40]1[CH:39]=[C:38]([C:35]2[CH:36]=[N:37][C:32]3[N:33]([C:12]([S:11][C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[CH:4]5)=[CH:13][N:31]=3)[N:34]=2)[CH:47]=[CH:46][C:41]=1[C:42]([O:44][CH3:45])=[O:43]

Participants

6

Reactant 4

HCID 8988D-ProlineHCID 31398ChlorosuccinimideHCID 67223257HCID 67223257, compoundHCID 86621502HCID 86621502, compound

Product 1

HCID 25145804HCID 25145804, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cooled (0° C.) mixture of (quinolin-6-ylthio)acetaldehyde (40.6 mg, 0.2 mmol) and D-proline (4.6 mg, 0.04 mmol) in chloroform (1.0 mL) was added N-chlorosuccinimide (26.7 mg, 0.2 mmol) with stirring. The mixture was stirred at 0° C. for 30 min, then gradually warmed to ambient temperature for 2 h. To the mixture was added methyl 4-(3-amino-1,2,4-triazin-6-yl)-2-fluorobenzoate (24.8 mg, 0.1 mmol). The reaction mixture was stirred for 1 h. The solvent was removed under reduced pressure. The residue was dissolved in isopropanol (2 mL) and heated to 100° C. overnight. After cooling, the mixture was filtered and the filtrate was purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=432.3.

Workup

  1. temperatureTo a cooled
  2. stirringThe mixture was stirred at 0° C. for 30 min
  3. stirringThe reaction mixture was stirred for 1 h
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in isopropanol (2 mL)
  6. temperatureheated to 100° C. overnight
  7. temperatureAfter cooling
  8. filtrationthe mixture was filtered
  9. customthe filtrate was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-6f68b776d7904588ba6cbb10c1b3c327
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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