Trifluoroacetic acid → HCID 59276173, compound

HRID 2070899Notes

Reaction equation

HRID 2070899 reaction equation
N[C:2]1[N:18]=[C:5]2[CH:6]=[CH:7][CH:8]=[C:9](CN3CCNC(=O)C3)[N:4]2N=1.FC(F)(F)C(O)=O.C(OC([N:33]([C:51](OC(C)(C)C)=O)[C:34]1[N:50]=[C:37]2[CH:38]=[CH:39][CH:40]=[C:41]([CH2:42][N:43]3[CH2:48][CH2:47][NH:46][C:45](=[O:49])[CH2:44]3)[N:36]2[N:35]=1)=O)(C)(C)C>ClCCl>[NH:4]1[C:5]2=[N:18][CH:2]=[C:51]([NH:33][C:34]3[N:50]=[C:37]4[CH:38]=[CH:39][CH:40]=[C:41]([CH2:42][N:43]5[CH2:48][CH2:47][NH:46][C:45](=[O:49])[CH2:44]5)[N:36]4[N:35]=3)[CH:6]=[C:7]2[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 68586804HCID 68586804, compoundHCID 68588090HCID 68588090, compound

Product 1

HCID 59276173HCID 59276173, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-((2-Amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)methyl)piperazin-2-one. Trifluoroacetic acid (2.55 mL, 33.1 mmol) was added to a stirred solution of N,N-di-tert-butoxycarbonyl-5-((3-oxopiperazinyl)methyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.740 g, 1.657 mmol) in dichloromethane (18.5 mL). The resulting solution was capped and stirred at room temperature for 23 h. Most of the solvent was removed on a rotary evaporator. The residue was loaded onto two 5 g Strata X—C ion exchange columns from Phenomenex. The columns were washed successively with acetonitrile, water, acetonitrile, methanol, and then 10% ammonium hydroxide in methanol. The product came off with the 10% ammonium hydroxide in methanol eluent. The 10% ammonium hydroxide in methanol eluent from both runs was concentrated on a rotary evaporator and dried under high vacuum at 40° C. to give the desired product (0.406 g, 1.649 mmol, 97%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 7.82 (br s, 1H), 7.43 (dd, J=7.42, 8.59 Hz, 1H), 7.28 (d, J=8.59 Hz, 1H), 6.92 (d, J=7.03 Hz, 1H), 6.03 (s, 2H), 3.94 (s, 2H), 3.21 (br s, 2H), 3.12 (s, 2H), 2.71 (t, 2H); MS (ESI) m/z 247.3 [M+1]+.

Workup

  1. customThe resulting solution was capped
  2. customMost of the solvent was removed on a rotary evaporator
  3. washThe columns were washed successively with acetonitrile, water, acetonitrile, methanol
  4. concentrationThe 10% ammonium hydroxide in methanol eluent from both runs was concentrated on a rotary evaporator
  5. customdried under high vacuum at 40° C.

Sources & evidence

ORD record
ord-f7fbd02835164ff1b27ccd4bd79b68ab
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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