Triethylamine → HCID 59631329, compound

HRID 1431700Notes

Reaction equation

HRID 1431700 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(N(CC)CC)C>C(#N)C.O.C(O)(=O)C>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([N:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]=1[CH3:12]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 59631329HCID 59631329, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

The 2,4-dichloro-5,7-difluoro-3-methylquinoline (300 mg, 1.20 mmol), (S)-tert-butyl pyrrolidine-2-carboxylate (620 mg, 3.60 mmol) and triethylamine (50 μL, 3.60 mmol) were combined in acetonitrile (7.6 mL). The mixture was then heated in a microwave reactor at 140° C. for 90 min. The reaction mixture was then cond to dryness and the residue was diluted with water (˜25 mL) and acetic acid (2 mL). This mixture was extracted with DCM (2×75 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL) and dried over magnesium sulfate. The filtrate was cond to obtain (S)-tert-butyl 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidine-2-carboxylate. Mass Spectrum (ESI) m/e=383.2 (M+1).

Workup

  1. extractionThis mixture was extracted with DCM (2×75 mL)
  2. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-7ee3e71642054f6ca595ab64b15578de
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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