Trifluoroacetic acid → HCID 53252274, compound

HRID 711456Notes

Reaction equation

HRID 711456 reaction equation
[F: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.C(O)(C(F)(F)F)=O>C(Cl)Cl>[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[F:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654708HCID 86654708, compound

Product 1

HCID 53252274HCID 53252274, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (1S,2R)-2-(7-fluoro-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (40.0 mg, 0.085 mmol) and TFA (2 mL, 26.0 mmol) in DCM (1 mL) was stirred at RT for 1 h. The mixture was concentrated and the resulting residue was purified by preparative HPLC to give the title compound as a white solid (20 mg, 63.5%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.36-1.97 (m, 8H), 2.30 (s, 3H), 3.70 (br s, 1H), 4.27 (br s, 1H), 4.33-4.46 (m, 2H), 6.73 (d, J=6.35 Hz, 1H), 6.79 (d, J=7.32 Hz, 1H), 7.17 (t, J=7.57 Hz, 1H), 7.43 (d, J=7.81 Hz, 1H), 7.46 (s, 1H), 7.76 (br s, 2H), 8.29 (s, 1H), 8.79 (s, 1H). [M+H] calc'd for C20H24FN5O, 370. found, 370.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-48e259f7b56c47269bee49f456e43279
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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