Trifluoroacetic acid → HCID 66744529, compound

HRID 1959461Notes

Reaction equation

HRID 1959461 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:10]=[CH:11][C:12]([N:36]2[CH2:41][C@H:40]3[C@H:38]([CH:39]3[C:42]([OH:44])=[O:43])[CH2:37]2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27](C(OC(C)(C)C)=O)[CH3:28])=[CH:22][CH:21]=2)=[N:18][N:19]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[N:10]=[CH:11][C:12]([N:36]2[CH2:37][C@H:38]3[C@H:40]([CH:39]3[C:42]([OH:44])=[O:43])[CH2:41]2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][NH:27][CH3:28])=[CH:22][CH:21]=2)=[N:18][N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66745061HCID 66745061, compound

Product 1

HCID 66744529HCID 66744529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,5S)-3-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (30 mg, 0.04 mmol) in DCM (0.3 mL) was added TFA (500 μL, 6.50 mmol) and reaction was stirred at room temperature for 2 h. The solvent was removed under reduced pressure and the residue was dissolved in DMSO, filtered and purified via reverse phase HPLC using a gradient of 10 to 99% MeOH—H2O (TFA modifier) to obtain (1R,5S)-3-[5-amino-6-[5-[4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid. LC/MS m/z 408.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.85 (s, 2H), 8.17 (d, J=8.2 Hz, 2H), 7.91 (s, 1H), 7.73 (d, J=8.2 Hz, 2H), 6.77 (s, 2H), 4.26 (t, J=5.7 Hz, 2H), 3.87 (d, J=10.4 Hz, 2H), 3.47-3.46 (m, 2H), 2.63 (t, J=5.2 Hz, 3H), 2.19 (s, 2H), 1.49 (t, J=2.9 Hz, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DMSO
  3. filtrationfiltered
  4. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-49e07db6e2124ad8b6e5be576b84f3ab
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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