Trifluoroacetic acid → HCID 53250672, compound

HRID 2092838Notes

Reaction equation

HRID 2092838 reaction equation
[Cl:1][C:2]1[C:3]2[CH2:33][NH:32][C:31](=[O:34])[C:4]=2[C:5]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15]C(=O)OC(C)(C)C.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>C(Cl)Cl>[C:37]([OH:39])([C:36]([F:41])([F:40])[F:35])=[O:38].[NH2:15][C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]1[NH:8][C:7]1[N:6]=[C:5]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)[C:4]2[C:31](=[O:34])[NH:32][CH2:33][C:3]=2[C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654727HCID 86654727, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 53250672HCID 53250672, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1S,2R)-2-(7-chloro-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (20 mg, 0.041 mmol) in DCM (0.8 mL) was added trifluoroacetic acid (0.31 mL). The reaction mixture was stirred at RT for 1 h, then concentrated to a brown residue which was diluted in MeOH (2 mL) and purified via preparative HPLC to give a TFA salt of the title compound as a fluffy white solid (12.3 mg, 61.9%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.85 (s, 1H), 8.36 (s, 1H), 7.83 (br s, 3H), 7.39-7.57 (m, 2H), 7.12-7.32 (m, 1H), 6.84 (d, J=7.6 Hz, 1H), 6.22 (d, J=6.8 Hz, 1H), 4.19-4.43 (m, 3H), 3.71 (br s, 1H), 2.32 (s, 3H), 1.37-1.99 (m, 8H). [M+H] calc'd for C20H24ClN5O, 386. found, 386.

Workup

  1. concentrationconcentrated to a brown residue which
  2. additionwas diluted in MeOH (2 mL)
  3. custompurified via preparative HPLC

Sources & evidence

ORD record
ord-8e6c8be185d04c9facf5a7946d6795f0
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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