Hydrochloric Acid → HCID 53251953, compound

HRID 515976Notes

Reaction equation

HRID 515976 reaction equation
[O:1]=[C:2]1[C:6]2[C:7]([NH:26][C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)=[N:8][C:9]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[NH:18]C(=O)OC(C)(C)C)=[CH:10][C:5]=2[CH2:4][NH:3]1.Cl.O1CCOCC1>>[NH2:18][C@H:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C@H:12]1[NH:11][C:9]1[N:8]=[C:7]([NH:26][C:27]2[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=2)[C:6]2[C:2](=[O:1])[NH:3][CH2:4][C:5]=2[CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86654728HCID 86654728, compound

Product 1

HCID 53251953HCID 53251953, compoundYield 25.7%

Procedure

A mixture of tert-butyl (1S,2R)-2-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (50.0 mg, 0.111 mmol) and 4N HCl in dioxane (2 mL, 8.00 mmol) was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure, the residue was purified by reverse phase preparative HPLC. The fractions were collected, concentrated, diluted with EtOAc, and basified with saturated aq NaHCO3 solution. The organic extract was dried and evaporated to give the title compound as a white solid (10 mg, 25.7%). 1H NMR (500 MHz, CDCl3) δ ppm 1.19-1.77 (m, 8 H), 2.29 (s, 3 H), 3.20 (br s, 1 H), 3.99 (br s, 1 H), 4.19 (s, 2 H), 6.06 (s, 1 H), 6.75 (d, J=7.32 Hz, 2H), 7.14 (t, J=7.81 Hz, 1 H), 7.48 (d, J=7.32 Hz, 1 H), 7.60 (s, 1 H), 7.90 (s, 1 H), 8.87 (s, 1 H). [M+H] calc'd for C20H25N5O, 352; found, 352.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase preparative HPLC
  3. customThe fractions were collected
  4. concentrationconcentrated
  5. additiondiluted with EtOAc
  6. extractionThe organic extract
  7. customwas dried
  8. customevaporated

Sources & evidence

ORD record
ord-bb2a4a25a80045ad8d9fb6103a34a7c9
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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