Trifluoroacetic acid → HCID 67030011, compound

HRID 1943127Notes

Reaction equation

HRID 1943127 reaction equation
[O:1]=[C:2]1[CH:12]=[N:11][CH:10]2[CH:13]3[N:3]1[CH2:4][CH:5]([CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:22]C(=O)OC(C)(C)C)[CH2:18][CH2:17]1)[N:6]3[C:7](=[O:14])[CH:8]=[CH:9]2.C(O)(C(F)(F)F)=O>ClCCl>[NH2:22][CH:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH:5]2[N:6]3[CH:13]4[CH:10]([CH:9]=[CH:8][C:7]3=[O:14])[N:11]=[CH:12][C:2](=[O:1])[N:3]4[CH2:4]2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86642087HCID 86642087, compound

Product 1

HCID 67030011HCID 67030011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl {1-[(3,8-dioxo-1,2,5a,8b-tetrahydro-3H,8H-2a,5,8a-triazaacenaphthylen-1-yl)methyl]-4-piperidinyl}carbamate (37 mg, 0.092 mmol) in anhydrous dichloromethane (2 ml) was treated with TFA (1 ml) and stirred at room temperature for 1 hour, evaporated to dryness, mixed with anhydrous dichloromethane and evaporated to a dark gum. This gum was dissolved in 1:1 dichloromethane:methanol (10 ml) and treated with MP-carbonate resin (600 mg) and stirred for 1.5 hours. The reaction was filtered and the resin was washed with 1:1 dichloromethane:methanol (30 ml) and the filtrate was evaporated to dryness. Purification on a 5 g SCX column eluting with a methanol to 2N methanolic ammonia gradient gave the product as a gum. Further evaporation from diethyl ether gave the product as a brown solid (22.8 mg, 82%).

Workup

  1. customevaporated to dryness
  2. additionmixed with anhydrous dichloromethane
  3. customevaporated to a dark gum
  4. dissolutionThis gum was dissolved in 1:1 dichloromethane
  5. additionmethanol (10 ml) and treated with MP-carbonate resin (600 mg)
  6. stirringstirred for 1.5 hours
  7. filtrationThe reaction was filtered
  8. washthe resin was washed with 1:1 dichloromethane
  9. custommethanol (30 ml) and the filtrate was evaporated to dryness
  10. customPurification on a 5 g SCX column
  11. washeluting with a methanol to 2N methanolic ammonia gradient

Sources & evidence

ORD record
ord-76b8d528266948faa783d644c744fbd3
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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