Trifluoroacetic acid → HCID 131734336, compound

HRID 1504883Notes

Reaction equation

HRID 1504883 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:17]=[C:18]([NH:25][C:26]2[N:31]=[C:30]([CH3:32])[C:29]([C:33]([OH:35])=[O:34])=[CH:28][CH:27]=2)[C:19]([C:22](=[O:24])[NH2:23])=[N:20][CH:21]=1)=O)(C)(C)C.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>ClCCl>[OH:42][C:36]([C:38]([F:41])([F:40])[F:39])=[O:37].[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:17]=[C:18]([NH:25][C:26]2[N:31]=[C:30]([CH3:32])[C:29]([C:33]([OH:35])=[O:34])=[CH:28][CH:27]=2)[C:19]([C:22](=[O:24])[NH2:23])=[N:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731758HCID 86731758, compound

Product 1

HCID 131734336HCID 131734336, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-{[5-({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)-2-carbamoylpyridin-3-yl]amino}-2-methylpyridine-3-carboxylic acid (49 mg, 0.10 mmol) in dichloromethane (1 mL) was added TFA (0.12 mL, 1.5 mmol), and the reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to afford 6-[(5-{[(1R,2S)-2-aminocyclohexyl]amino}-2-carbamoylpyridin-3-yl)amino]-2-methylpyridine-3-carboxylic acid TFA salt. MS ESI calc'd. for C19H25N6O3 [M+H]+ 385. found 385. 1H NMR (500 MHz, DMSO-d6) δ 12.73 (s, 1H), 12.22 (s, 1H), 8.67 (s, 1H), 8.05 (d, J=8.6 Hz, 1H), 8.01 (s, 1H), 7.85 (s, 3H), 7.76 (s, 1H), 7.48 (s, 1H), 6.73 (d, J=8.6 Hz, 1H), 6.45 (d, J=7.8 Hz, 1H), 3.93-3.77 (m, 1H), 3.64-3.49 (m, 1H), 2.72 (s, 3H), 1.94-1.79 (m, 2H), 1.79-1.70 (m, 1H), 1.71-1.50 (m, 3H), 1.51-1.36 (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-a598cff081264e5b9eabe1ad22705dc9
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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