Water → HCID 66958618, compound

HRID 1984518Notes

Reaction equation

HRID 1984518 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[CH2:25][C:26]1[N:30]([CH3:31])[N:29]=[C:28]([C:32]([NH2:34])=O)[CH:27]=1.C(N(CC)CC)C.O>ClCCl.CCCCCC>[O:24]=[C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](=[O:14])[N:16]1[CH2:25][C:26]1[N:30]([CH3:31])[N:29]=[C:28]([C:32]#[N:34])[CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 66958823HCID 66958823, compound

Product 1

HCID 66958618HCID 66958618, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of trifluoroacetic anhydride (0.996 mL, 7.05 mmol) in dichloromethane (15 mL) was added slowly to a 0° C. solution of 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-methyl-1H-pyrazole-3-carboxamide (1.67 g, 5.87 mmol) and triethylamine (1.78 g, 17.6 mmol) in dichloromethane (15 mL). The resulting solution was stirred for 30 minutes, and water (50 mL) was added. The work-up procedure described in Part D of Example 64 was followed. Hexane (100 mL) was added to the resulting off-white solid, which was isolated by filtration and washed with hexane. The resulting light-brown solid was purified by chromatography using a HORIZON HPFC system (40M cartridge, eluting with 1% to 10% CMA in chloroform) to provide 1.57 g of 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-methyl-1H-pyrazole-3-carbonitrile as an off-white solid.

Workup

  1. customwhich was isolated by filtration
  2. washwashed with hexane
  3. customThe resulting light-brown solid was purified by chromatography
  4. washa HORIZON HPFC system (40M cartridge, eluting with 1% to 10% CMA in chloroform)

Sources & evidence

ORD record
ord-ad05b2fe1147495a808eb9c59537f017
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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