tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate → 2-[(7-Amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1181291Notes

Reaction equation

HRID 1181291 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:19]=[C:9]2[N:10]=[C:11](S(C)(=O)=O)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1.[NH2:20][CH2:21][C@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>CC#N>[C:30]([O:29][C:27]([N:23]1[CH2:24][CH2:25][CH2:26][CH:22]1[CH2:21][NH:20][C:11]1[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:19]=[C:9]2[N:10]=1)=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 1512534tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 99708822-(Furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine

Product 1

HCID 694333622-[(7-Amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 87.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (2.5 mmol; see Example 1(a)) was suspended in 20 mL of CH3CN along with 5 mmol of (R)-2-aminomethyl-1-Boc-pyrrolidine (Astatech, Monmouth Junction, N.J.). The reaction mixture was stirred under reflux for 2 hours. It was then cooled to room temperature and concentrated under reduced pressure. The resulting residue was diluted with CH2Cl2 and washed with dilute 1% citric acid, brine, dried with Na2SO4 and concentrated under reduced pressure. Purification by chromatography (98% CH2Cl2, 2% MeOH) afforded 880 mg of 2-[(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting residue was diluted with CH2Cl2
  4. washwashed
  5. additionwith dilute 1% citric acid, brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by chromatography (98% CH2Cl2, 2% MeOH)

Sources & evidence

ORD record
ord-8a3a44f9a3bb45f4ae5ff06683b0714f
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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