HCID 118598561, compound → HCID 118599084, compound

HRID 1050396Notes

Reaction equation

HRID 1050396 reaction equation
COC1C=CC(COC2C(=O)[N:13]3[C:16]4(CCCCC4)[NH:17][C:18](=[O:19])[C:12]3=[C:11]([CH3:25])C=2)=CC=1.[CH2:28]([Li])CCC.Cl[C:34]1[CH:39]=[C:38](NC2N=CN=C(NC(C3CC3)=O)C=2)[C:37](=[O:53])[N:36]2[C:54]([C:59]3[CH:64]=[CH:63][CH:62]=C(F)C=3)([CH3:58])[NH:55][C:56](=[O:57])[C:35]=12>O1CCCC1>[CH3:28][C:34]1[CH:39]=[C:38]([C:18]([C:12]2[CH:11]=[CH:25][N:17]=[CH:16][N:13]=2)=[O:19])[C:37](=[O:53])[N:36]2[C:54]3([CH2:58][CH2:62][CH2:63][CH2:64][CH2:59]3)[NH:55][C:56](=[O:57])[C:35]=12

Participants

5

Reactant 3

HCID 118598561HCID 118598561, compoundHCID 118598862HCID 118598862, compoundHCID 178418339Butyllithium

Product 1

HCID 118599084HCID 118599084, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6′-bromo-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-c]pyridine]-1′,5′-dione (2, 2 g, 6.43 mmol) in tetrahydrofuran (30 mL) at −78° C. is added n-butyllithium (1.6 M in hexanes, 12.06 mL, 19.29 mmol) dropwise, followed by N-methoxy-N-methylpyrimidine-4-carboxamide (1, 1.29 g, 7.72 mmol). The reaction is slowly warmed to room temperature and stirred for 4 h. The reaction is quenched via the slow addition of water. The mixture is warmed to room temperature and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated. The crude is purified via column chromatography to afford 8′-methyl-6′-(pyrimidine-4-carbonyl)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (3).

Workup

  1. customThe reaction is quenched via the slow addition of water
  2. temperatureThe mixture is warmed to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude is purified via column chromatography

Sources & evidence

ORD record
ord-c09c20fbce0a40faad4ac8bdec2f9d8a
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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