Triethylamine → HCID 117933012, compound

HRID 1477642Notes

Reaction equation

HRID 1477642 reaction equation
[NH2:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH:4]=[C:3]1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.O1CCCC1>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:3]2[CH:2]([NH:1][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH:4]=2)=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 117839662HCID 117839662, compound

Product 1

HCID 117933012HCID 117933012, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (2.0 mL) of tert-butyl 5-amino-4-(4-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (100 mg, 0.342 mmol) synthesized in Reference Synthesis Example 202, triethylamine (52.0 μL, 0.374 mmol), and N,N-dimethyl-4-aminopyridine (2.00 mg, 0.0170 mmol) were added, and then methanesulfonyl chloride (29.0 μL, 0.374 mmol) was added at 0° C. with stirring, followed by stirring the resultant reaction solution for 2 hours. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product of the title compound.

Workup

  1. additionwere added
  2. stirringby stirring the resultant
  3. customreaction solution for 2 hours
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fddf5701cdf449949f85607c22b1e2b8
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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