Trifluoroacetic acid → HCID 67496586, compound

HRID 1628308Notes

Reaction equation

HRID 1628308 reaction equation
[NH2:1][C:2]1[O:6][C:5]([C:7]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][N:11]3[C:22](=[O:35])[C@@H:23]([NH:31]C(=O)[O-])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:31][C@@H:23]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:22]([N:11]1[C:12]2[C:8](=[C:7]([C:5]3[O:6][C:2]([NH2:1])=[N:3][N:4]=3)[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:13]=2)[CH2:9][CH2:10]1)=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86664841HCID 86664841, compound

Product 1

HCID 67496586HCID 67496586, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 ml flask containing (S)-1-(4-(5-amino-1,3,4-oxadiazol-2-yl)-6-(pyridin-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate was added 20 ml of DCM and 10 ml of TFA. The reaction was stirred at room temperature for 6 hours at which time the solvent was removed with a stream of nitrogen to give (2S)-2-amino-1-(4-(5-amino-1,3,4-oxadiazol-2-yl)-6-(pyridin-4-yl)indolin-1-yl)-3-phenylpropan-1-one 59 (98 mg, 100% yield) as a white solid LCMS ESI (pos.) m/e: 427.1 (M+1): 1H NMR (400 MHz, DMSO-d6) δ ppm 8.76 (d, J=6.26 Hz, 2H), 8.58 (d, J=1.56 Hz, 1H), 8.36 (br. s., 3H), 7.71-7.81 (m, 3H), 7.22-7.41 (m, 7H), 4.55 (br. s., 1H), 4.31 (td, J=10.37, 6.65 Hz, 1H), 3.68 (td, J=10.27, 6.46 Hz, 1H), 3.33-3.50 (m, 1H), 3.08-3.28 (m, 3H).

Workup

  1. customwas removed with a stream of nitrogen

Sources & evidence

ORD record
ord-6b43d0c80ba743ba8aa60c644c30002b
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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