HCID 59233383, compound → HCID 59233384, compound

HRID 1400088Notes

Reaction equation

HRID 1400088 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[N:5][C:4]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17](C(O)=O)[CH2:16][CH2:15]1.C(OC(N1CCC(NC2N=NC(C(F)(F)F)=CC=2OC)CC1)=O)(C)(C)C>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[N:6]=[N:5][C:4]=1[NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 59233383HCID 59233383, compoundHCID 68720318HCID 68720318, compound

Product 1

HCID 59233384HCID 59233384, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(4-Methoxy-6-trifluoromethyl-pyridazin-3-ylamino)-piperidine-1-carboxylic acid tent-butyl ester (D7) (0.73 g, 1.93 mmol) and Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (2.35 g, 9.65 mmol) in methanol (20 ml) was shaken at room temperature for 18 h. After this period, the mixture was filtered and then a 7M solution of ammonia in methanol was added. The mixture was shaken for 1 h, filtered and the filtrate evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. to yield D8 (0.49 g, 92%) as a yellow syrup. C11H15F3N4O requires 276; Found 277 (MH+).

Workup

  1. waitAfter this period
  2. filtrationthe mixture was filtered
  3. additiona 7M solution of ammonia in methanol was added
  4. stirringThe mixture was shaken for 1 h
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-a3b20e1d4989429ca69ccf8517eff897
Source dataset
uspto-grants-2014_12
Patent number
US08906921B2

Reaction notes

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