Trifluoroacetic acid → HCID 86731759, compound

HRID 1504885Notes

Reaction equation

HRID 1504885 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(=O)OC(C)(C)C)=[CH:6][C:5]=1[NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:36])[N:33]([CH3:35])[CH3:34])=[C:28]([CH3:37])[N:27]=1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl>[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]=[CH:30][C:29]([C:32](=[O:36])[N:33]([CH3:34])[CH3:35])=[C:28]([CH3:37])[N:27]=2)[C:4]([C:1]([NH2:2])=[O:3])=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731757HCID 86731757, compound

Product 1

HCID 86731759HCID 86731759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {(1S,2R)-2-[(6-carbamoyl-5-{[5-(dimethylcarbamoyl)-6-methylpyridin-2-yl]amino}pyridin-3-yl)amino]cyclohexyl}carbamate (48 mg, 0.094 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (0.10 mL, 1.3 mmol). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and purified by reverse phase HPLC to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-{[5-(dimethylcarbamoyl)-6-methylpyridin-2-yl]amino}pyridine-2-carboxamide. MS ESI calc'd. for C21H30N7O2 [M+H]+ 412. found 412. 1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.55 (d, J=2.3 Hz, 1H), 7.91 (s, 1H), 7.69 (d, J=2.3 Hz, 1H), 7.45 (d, J=. 8.4 Hz, 1H), 7.33 (s, 1H), 6.67 (d, J=8.4 Hz, 1H), 6.62 (d, J=7.0 Hz, 1), 3.63-3.50 (m, 1H), 3.37-3.27 (m, 1H), 2.99 (s, 3H), 2.82 (s, 3H), 2.34 (s, 3H), 1.88-1.72 (m, 2H), 1.69-1.50 (m, 4H), 1.48-1.31 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-f2ecb028f75a490bb9fd22a286ae579f
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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