Trifluoroacetic acid → HCID 178429072, compound

HRID 1504874Notes

Reaction equation

HRID 1504874 reaction equation
[C:1]([C:4]1[N:9]=[CH:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17][C:18](=[O:24])[O:19]C(C)(C)C)=[CH:6][C:5]=1[NH:25][C:26]1[CH:31]=[C:30]([OH:32])[CH:29]=[C:28]([CH3:33])[N:27]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:18]([OH:24])=[O:19].[NH2:17][C@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:7]1[CH:6]=[C:5]([NH:25][C:26]2[CH:31]=[C:30]([OH:32])[CH:29]=[C:28]([CH3:33])[N:27]=2)[C:4]([C:1]([NH2:2])=[O:3])=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178429073HCID 178429073, compound

Product 1

HCID 178429072HCID 178429072, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(1S,2R)-2-({6-carbamoyl-5-[(4-hydroxy-6-methylpyridin-2-yl)amino]pyridin-3-yl]amino)cyclohexyl}carbamate (32 mg, 0.070 mmol) in DCM (2 ml) was added TFA (1.0 mL, 13 mmol), and the reaction mixture was stirred for 30 minutes at ambient temperature. The reaction mixture was concentrated under reduced pressure, dissolved in DMSO (1 mL), and purified by reverse phase HPLC (acetonitrile/water with 0.1% formic acid, linear gradient) to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4-hydroxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide formic acid salt. MS ESI calc'd. for C18H25N6O2 [M+H]+ 357. found 357. 1H NMR (500 MHz, CD3OD) δ 8.10 (s, 1H), 7.85 (s, 1H), 7.40 (s, 1H), 6.39 (s, 1H), 6.25 (s, 1H), 3.95 (br s, 1H), 3.56 (br s, 1H), 2.38 (s, 3H), 1.90-1.82 (m, 3H), 1.80-1.62 (m, 3H), 1.60-1.50 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in DMSO (1 mL)
  3. custompurified by reverse phase HPLC (acetonitrile/water with 0.1% formic acid, linear gradient)

Sources & evidence

ORD record
ord-1cf0ae99d20a4fffac283055058eb74e
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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