Trifluoroacetic acid → HCID 118036501, compound

HRID 1778105Notes

Reaction equation

HRID 1778105 reaction equation
C([O:5][CH2:6][CH2:7][NH:8][C:9]1[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([NH:17][C:18]([N:20]2[C:29]3[C:24](=[CH:25][C:26]([CH2:32][N:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][C:34]4=[O:40])=[C:27]([CH:30]=[O:31])[N:28]=3)[CH2:23][CH2:22][CH2:21]2)=[O:19])[CH:10]=1)(C)(C)C.C(C(O)=O)(F)(F)F>C(Cl)Cl>[C:15]([C:14]1[C:9]([NH:8][CH2:7][CH2:6][OH:5])=[CH:10][C:11]([NH:17][C:18]([N:20]2[C:29]3[C:24](=[CH:25][C:26]([CH2:32][N:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][C:34]4=[O:40])=[C:27]([CH:30]=[O:31])[N:28]=3)[CH2:23][CH2:22][CH2:21]2)=[O:19])=[N:12][CH:13]=1)#[N:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118036691HCID 118036691, compound

Product 1

HCID 118036501HCID 118036501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-((2-(tert-butoxy)ethyl)amino)-5-cyanopyridin-2-yl)-7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (Example 196, 1.11 g, 2.02 mmol) in DCM (10 ml) was treated with CF3CO2H (1.56 ml, 20.23 mmol). The reaction mixture was stirred for 48 h. The reaction was quenched by addition of saturated Na2CO3 solution. The reaction mixture was stirred for 16 h. The aqueous was extracted with DCM (×2) and the combined organic extracts were concentrated under reduced pressure. The solid was dissolved in a minimum amount of DCM with a drop of MeOH, then Et2O was added to give a precipitate which was filtered. The solid was triturated with Et2O and filtered to afford the title compound.

Workup

  1. customThe reaction was quenched by addition of saturated Na2CO3 solution
  2. stirringThe reaction mixture was stirred for 16 h
  3. extractionThe aqueous was extracted with DCM (×2)
  4. concentrationthe combined organic extracts were concentrated under reduced pressure
  5. dissolutionThe solid was dissolved in a minimum amount of DCM with a drop of MeOH
  6. additionEt2O was added
  7. customto give a precipitate which
  8. filtrationwas filtered
  9. customThe solid was triturated with Et2O
  10. filtrationfiltered

Sources & evidence

ORD record
ord-363ff95638e94de28742a773721a01f8
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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