Trifluoroacetic acid → 6-((1R,2S)-2-Aminocyclohexylamino)-4-(4-fluoro-3-methylphenylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 515989Notes

Reaction equation

HRID 515989 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]3[C:15](=[O:18])[NH:16][CH2:17][C:13]=3[CH:12]=[C:11]([NH:19][C@@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]3[NH:26]C(=O)OC(C)(C)C)[N:10]=2)=[CH:4][C:3]=1[CH3:34].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:26][C@H:21]1[CH2:22][CH2:23][CH2:24][CH2:25][C@H:20]1[NH:19][C:11]1[N:10]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH3:34])[CH:4]=2)[C:14]2[C:15](=[O:18])[NH:16][CH2:17][C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654707tert-Butyl (1S,2R)-2-(4-(4-fluoro-3-methylphenylamino)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

Product 1

HCID 532522736-((1R,2S)-2-Aminocyclohexylamino)-4-(4-fluoro-3-methylphenylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneYield 2.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (1S,2R)-2-(4-(4-fluoro-3-methylphenylamino)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (50.0 mg, 0.106 mmol) and TFA (1 mL, 12.98 mmol) in DCM (0.5 mL) was stirred at RT for 1 hr. The resulting mixture was concentrated and the residue was purified by preparative HPLC to give the title compound as a white solid (1 mg, 2.54%). 1H NMR (500 MHz, CD3OD) δ ppm 1.14-1.95 (m, 8 H), 2.28 (s, 3 H), 3.73 (br s, 1 H), 4.30 (s, 2H), 4.38 (s, 1 H), 6.17 (s, 1 H), 7.00 (t, J=9.03 Hz, 1 H), 7.41-7.54 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-145c07d5ddb94bb5b364a685d636192d
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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