Dimethylformamide → HCID 58851604, compound

HRID 2042086Notes

Reaction equation

HRID 2042086 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[C:20](OS(C(F)(F)F)(=O)=O)[CH:19]=[CH:18]3)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].CN.Cl.C[CH2:37][N:38](CC)CC.CN(C=O)C>[Cl-].[Na+].O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[C:20]([NH:38][CH3:37])[CH:19]=[CH:18]3)[N:6]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 6364545Methylamine hydrochloride2×HCID 58851274HCID 58851274, compound

Product 1

HCID 58851604HCID 58851604, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl 3-t-butyl-1-(2-(trifluoromethylsulfonyloxy)quinolin-6-yl)-1H-pyrazole-5-carboxylate (see WO 2006/071940A2, 0.380 g, 0.806 mmol), MeNH2.HCl (0.109 g, 1.61 mmol) and Et3N (0.449 ml, 3.22 mmol) were combined DMF (8 mL) and stirred at RT overnight. Additional portions of MeNH2.HCl (0.109 g, 1.61 mmol) and Et3N (0.449 ml, 3.22 mmol) were added and the reaction was stirred an additional 4 h at RT and 3 h at 60° C. The completed reaction was diluted with brine and extracted with EtOAc. The extracts were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography to provide ethyl 3-tert-butyl-1-(2-(methylamino)quinolin-6-yl)-1H-pyrazole-5-carboxylate (240 mg, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.90 (d, J=9.2 Hz, 1H), 7.68 (d, J=2.8 Hz, 1H), 7.53 (d, J=9.2 Hz, 1H), 7.46 (dd, J=8.8, 2.0 Hz, 1H), 7.17 (q, J=4.8 Hz, 1H), 6.98 (s, 1H), 6.80 (d, J=8.8 Hz, 1H), 4.16 (q, J=7.2 Hz, 2H), 2.92 (d, J=4.8 Hz, 3H), 1.32 (s, 9H), 1.13 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 353.2 (M+H+).

Workup

  1. stirringthe reaction was stirred an additional 4 h at RT and 3 h at 60° C
  2. customThe completed reaction
  3. extractionextracted with EtOAc
  4. washThe extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-cf0d199f4f4448adaaa05017f5f27c0a
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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