Trifluoroacetic acid → 5-[(3-aminopropyl)amino]-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt

HRID 1504881Notes

Reaction equation

HRID 1504881 reaction equation
COC1C=CC(C([NH:18][C:19]([C:21]2[N:26]=[CH:25][C:24]([NH:27][CH2:28][CH2:29][CH2:30][NH:31]C(=O)OC(C)(C)C)=[CH:23][C:22]=2[NH:39][C:40]2[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[N:41]=2)=[O:20])C2C=CC(OC)=CC=2)=CC=1.C([SiH](CC)CC)C.[C:55]([OH:61])([C:57]([F:60])([F:59])[F:58])=[O:56]>ClCCl>[OH:61][C:55]([C:57]([F:60])([F:59])[F:58])=[O:56].[NH2:31][CH2:30][CH2:29][CH2:28][NH:27][C:24]1[CH:23]=[C:22]([NH:39][C:40]2[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[N:41]=2)[C:21]([C:19]([NH2:18])=[O:20])=[N:26][CH:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86731751Tert-butyl {3-[(6-{[bis(4-methoxyphenyl)methyl]carbamoyl}-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl)amino]propyl}carbamate

Product 1

HCID 867317525-[(3-aminopropyl)amino]-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {3-[(6-{[bis(4-methoxyphenyl)methyl]carbamoyl}-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl)amino]propyl}carbamate (51 mg, 0.080 mmol) in dichloromethane (4 mL) was added triethylsilane (0.064 mL, 0.40 mmol) followed by TFA (0.8 mL) at ambient temperature. After 2 hours, the reaction mixture was concentrated under reduced pressure, and the residue was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to afford 5-[(3-aminopropyl)amino]-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt. MS ESI calc'd. for C16H23N6O [M+H]+ 315. found 315. 1H NMR (500 MHz, DMSO-d6) δ 11.74 (s, 1H), 8.22-8.04 (br s, 1H), 7.92-7.76 (m, 4H), 7.58 (s, 1H), 7.37 (s, 1H), 6.74-6.66 (br s, 2H), 3.22-3.16 (m, 2H), 2.94-2.84 (m, 2H), 2.40 (s, 3H), 2.25 (s, 3H), 1.90-1.82 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)

Sources & evidence

ORD record
ord-3b879b7d20024498b6302966114686da
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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