Ammonium Hydroxide → HCID 69679484, compound

HRID 1594233Notes

Reaction equation

HRID 1594233 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]2[CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:16]=[CH:17][C:11]=2[C:10]=1[C:25]([OH:27])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)([N:30]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:13][C:12]2[CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:16]=[CH:17][C:11]=2[C:10]=1[C:25](=[O:27])[NH2:30])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 69337769HCID 69337769, compound

Product 1

HCID 69679484HCID 69679484, compoundYield 32.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1g (150 mg, 0.38 mmol) in DMF (3 mL) was added 1,1′-carbonyl diimidazole (125 mg, 0.78 mmol). The resultant solution was stirred at room temperature for 1 h and mixed with ammonium hydroxide (37%, 5 mL). The mixture was diluted with brine solution (10 mL) and extracted with ethyl acetate (20 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 1:1) then provided the title compound (48 mg, 32%) as a white solid: MS (ES) m/z 387 (M+H)+; 1H NMR (400 MHz, CDCl3) δ11.14 (s, 1H), 7.94 (s, 1H), 7.85 (d, J=4.4 Hz, 1H), 7.61 (m, 3H), 7.18 (m, 2H), 5.87 (brs, 2H), 1.59 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate (20 mL, 3×)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0bdfee0a0873451f83bf60721c143231
Source dataset
uspto-grants-2007_11
Patent number
US07300952B2

Reaction notes

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