Trifluoroacetic acid → 5-{[3-(acetylamino)-2-aminopropyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt
Reaction equation
[C:1]([NH:4][CH2:5][CH:6]([NH:44]C(=O)OC(C)(C)C)[CH2:7][NH:8][C:9]1[CH:10]=[N:11][C:12]([C:24](=[O:43])[NH:25]C(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)=[C:13]([NH:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[N:17]=2)[CH:14]=1)(=[O:3])[CH3:2].[C:52]([OH:58])([C:54]([F:57])([F:56])[F:55])=[O:53].C([SiH](CC)CC)C>C(Cl)Cl>[OH:58][C:52]([C:54]([F:57])([F:56])[F:55])=[O:53].[C:1]([NH:4][CH2:5][CH:6]([NH2:44])[CH2:7][NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[N:17]=2)[C:12]([C:24]([NH2:25])=[O:43])=[N:11][CH:10]=1)(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl {1-(acetylamino)-3-[(6-{[bis(4-methoxyphenyl)methyl]carbamoyl}-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl)amino]propan-2-yl}carbamate in DCM (1 mL) were added TFA (0.2 mL) and triethylsilane (0.146 mL, 0.917 mmol). The reaction mixture was stirred at room temperature for 4 hours, and then concentrated under reduced pressure. The residue was purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to give 5-{[3-(acetylamino)-2-aminopropyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt. MS ESI calc'd for C18H26N7O2 [M+H]+ 372. found 372. 1H NMR (500 MHz, CD3OD) δ 7.84 (d, J=2 Hz, 1H), 7.41 (s, 1H), 7.21 (s, 1H), 6.95 (s, 1H), 3.60-3.42 (m, 5H), 2.54 (s, 3H), 2.43 (s, 3H), 1.99 (s, 3H).
Workup
- concentrationconcentrated under reduced pressure
- customThe residue was purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)
Sources & evidence
- ORD record
- ord-5e9adf58e2a14224807cea9e0199c836
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216173B2
Reaction notes
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