Trifluoroacetic acid → HCID 66744512, compound

HRID 1959459Notes

Reaction equation

HRID 1959459 reaction equation
[CH2:1]([S:3]([NH:6][CH:7]1[C@@H:11]2[CH2:12][N:13]([C:15]3[N:20]=[C:19]([C:21]4[O:25][C:24]([C:26]5[CH:31]=[CH:30][C:29]([CH2:32][N:33](C)[C:34](=O)OC(C)(C)C)=[CH:28][CH:27]=5)=[N:23][N:22]=4)[C:18]([N:42](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:17][CH:16]=3)[CH2:14][C@@H:10]2[CH2:9][CH2:8]1)(=[O:5])=[O:4])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:42][C:18]1[N:17]=[CH:16][C:15]([N:13]2[CH2:14][C@@H:10]3[CH2:9][CH2:8][CH:7]([NH:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[C@@H:11]3[CH2:12]2)=[N:20][C:19]=1[C:21]1[O:25][C:24]([C:26]2[CH:27]=[CH:28][C:29]([CH2:32][NH:33][CH3:34])=[CH:30][CH:31]=2)=[N:23][N:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66744601HCID 66744601, compound

Product 1

HCID 66744512HCID 66744512, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N-[[4-[5-[6-[(3aR,6aS)-6-(ethylsulfonylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-3-[bis(tert-butoxycarbonyl)amino]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (110 mg, 0.14 mmol) in DCM (1 mL) was treated with TFA (1.0 g, 676 μL, 8.8 mmol). The reaction mixture was stirred for 1 hour. The solvent was evaporated and the residue was purified via reverse phase HPLC using 10 to 99% ACN in water (5 mM HCl modifier) to obtain N-[(3aR,6aS)-2-[5-amino-6-[5-[4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-6-yl]ethanesulfonamide. LC/MS m/z 499.2 [M+H]+

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified via reverse phase

Sources & evidence

ORD record
ord-a32f1025b1344f75b60ff2c37c7df92a
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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