Trifluoroacetic acid → HCID 66745103, compound

HRID 1959473Notes

Reaction equation

HRID 1959473 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:26]2[O:30][C:29]([C:31]3[CH:36]=[CH:35][C:34]([CH2:37][N:38](C)[C:39](=O)OC(C)(C)C)=[CH:33][CH:32]=3)=[N:28][N:27]=2)=[N:11][C:12]([C:15]2[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:25])[CH2:23][CH3:24])[CH2:17][CH:16]=2)=[CH:13][N:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:25])[CH2:23][CH3:24])[CH2:17][CH:16]=2)=[N:11][C:10]=1[C:26]1[O:30][C:29]([C:31]2[CH:32]=[CH:33][C:34]([CH2:37][NH:38][CH3:39])=[CH:35][CH:36]=2)=[N:28][N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66744330HCID 66744330, compound

Product 1

HCID 66745103HCID 66745103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-[4-(propanoylamino)cyclohexen-1-yl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (21 mg, 0.03 mmol) in DCM (220 μL) was added TFA (326 mg, 220 μL, 2.9 mmol) and the reaction mixture was stirred for 40 minutes at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DMF (1 mL) and purified by Gilson reverse phase HPLC using (5-99% ACN/H2O (5 mM HCl)) to yield N-(4-(5-Amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)cyclohex-3-enyl)propionamide. 1H NMR (400 MHz, MeOD) d 8.41 (s, 1H), 8.31 (d, J=8.4 Hz, 2H), 7.77 (d, J=8.3 Hz, 2H), 6.64 (s, 1H), 4.34 (s, 2H), 4.11-3.98 (m, 1H), 2.81 (s, 4H), 2.63 (d, J=17.8 Hz, 2H), 2.26 (q, J=7.7 Hz, 3H), 2.15-2.04 (m, 1H), 1.78 (dd, J=11.3, 5.0 Hz, 1H), 1.18 (t, J=7.6 Hz, 3H). LC/MS m/z 434.2 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DMF (1 mL)
  3. custompurified by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-a537d8285c214a7ebb058d5b0a217c35
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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