HCID 59233381, compound → HCID 59233379, compound

HRID 1400082Notes

Reaction equation

HRID 1400082 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12](C(O)=O)[CH2:11][CH2:10]2)=[C:4]([O:18][CH3:19])[CH:3]=1.C(OC(N1CCC(NC2N=NC(Cl)=CC=2OC)CC1)=O)(C)(C)C>CO>[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[C:4]([O:18][CH3:19])[CH:3]=1

Participants

4

Reactant 2

HCID 59233381HCID 59233381, compoundHCID 86639794HCID 86639794, compound

Product 1

HCID 59233379HCID 59233379, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(6-chloro-4-methoxy-pyridazin-3-ylamino)-piperidine-1-carboxylic acid tent-butyl ester (D1) (0.44 g, 1.27 mmol) and Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (1.55 g, 6.35 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 D2 (0.25 g, 81%) as a white solid. C10H15ClN4O requires 242; Found 243 (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-fae47e9e66be4c43b0bbc028bcc48244
Source dataset
uspto-grants-2014_12
Patent number
US08906921B2

Reaction notes

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