Water → HCID 66958618, compound

HRID 2283918Notes

Reaction equation

HRID 2283918 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-ad527ceedd6944e88c730acb324aa2d5
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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