Tetrahydrofuran ethyl acetate → HCID 53250218, compound

HRID 2092811Notes

Reaction equation

HRID 2092811 reaction equation
[CH2:1]([O:3][CH2:4][C@H:5]([NH:26]C(=O)OC(C)(C)C)[CH2:6][NH:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[C:11]2[C:22](=[O:25])[NH:23][CH2:24][C:10]=2[CH:9]=1)[CH3:2].CCOC(C)=O.C1COCC1>C(Cl)Cl>[NH2:26][C@@H:5]([CH2:4][O:3][CH2:1][CH3:2])[CH2:6][NH:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[C:11]2[C:22](=[O:25])[NH:23][CH2:24][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 21939870Tetrahydrofuran ethyl acetateHCID 67239348HCID 67239348, compound

Product 1

HCID 53250218HCID 53250218, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 1-ethoxy-3-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)propan-2-ylcarbamate (109 mg, 0.239 mmol) in DCM (1 mL) was added a TFA/DCM solution (1/1, 10 mL). The mixture was stirred at RT for 2 h. After removal of the solvent, the resulting crude material was reconstituted in a solution of MeOH/DCM (1/1, 5 mL) and was purified via reverse phase preparative HPLC. The fractions were collected, and ACN was removed via rotary evaporation. The resulting aq solution was neutralized with saturated aq NaHCO3, washed with EtOAc (2×200 mL), dried over Na2SO4, and filtered. The organic phase was stripped to dryness via rotary evaporation to give the title compound (11 mg, 13%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08-1.18 (m, 3H), 1.25-1.44 (m, 4H), 2.26-2.32 (m, 3H), 4.07-4.17 (m, 3H), 4.19-4.29 (m, 2H), 6.03 (s, 1H), 6.78 (d, J=7.83 Hz, 1H), 7.06 (br s, 1H), 7.12-7.22 (m, 1H), 7.48 (s, 1H), 7.60 (d, J=7.83 Hz, 1H), 7.66-7.75 (m, 2H), 7.99 (s, 1H), 8.83-8.97 (m, 1H). [M+H] calc'd for C19H25N5O2, 356; found, 356.

Workup

  1. customAfter removal of the solvent
  2. customwas purified via reverse phase preparative HPLC
  3. customThe fractions were collected
  4. customACN was removed via rotary evaporation
  5. washwashed with EtOAc (2×200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customThe organic phase was stripped to dryness via rotary evaporation

Sources & evidence

ORD record
ord-d72498763150486aa3aa3825b1b4ed8c
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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