(R)-2-(2-(2,4-Dimethoxybenzyl)-7-fluoro-4-(furan-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide → (R)-2-(7-Fluoro-4-(furan-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide

HRID 711574Notes

Reaction equation

HRID 711574 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:14][C:13]2[C:12]([F:15])=[C:11]([NH:16][C@H:17]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:18]([NH2:20])=[O:19])[N:10]=[C:9]([C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)[C:8]=2[C:7]1=[O:30]>C(O)(C(F)(F)F)=O>[F:15][C:12]1[C:13]2[CH2:14][NH:6][C:7](=[O:30])[C:8]=2[C:9]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)=[N:10][C:11]=1[NH:16][C@H:17]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:18]([NH2:20])=[O:19]

Participants

3

Reactant 1

HCID 58317552(R)-2-(2-(2,4-Dimethoxybenzyl)-7-fluoro-4-(furan-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide

Product 1

HCID 58317542(R)-2-(7-Fluoro-4-(furan-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-2-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(furan-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide (93.1 mg, 0.188 mmol) in TFA (5 mL) was heated to 65° C. for 3 h. The solvent was removed and the resulting residue was diluted in MeOH/DCM (10 mL) and was purified via preparative HPLC eluting with water (0.05% TFA) and ACN (30%, 0.035% TFA). The collected fractions were stripped to dryness via rotary evaporation to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.79-0.97 (m, 6H), 1.52-1.87 (m, 3H), 4.38 (s, 2H), 4.66-4.85 (m, 1H), 6.61 (dd, J=3.54, 1.77 Hz, 1H), 6.92-7.07 (m, 2H), 7.36 (br s, 1H), 7.79 (dd, J=1.64, 0.63 Hz, 1H), 8.04 (dd, J=3.54, 0.51 Hz, 1H), 8.32 (s, 1H). [M+H] calc'd for C17H19FN4O3, 347. found, 347.

Workup

  1. customThe solvent was removed
  2. additionthe resulting residue was diluted in MeOH/DCM (10 mL)
  3. customwas purified via preparative HPLC
  4. washeluting with water (0.05% TFA) and ACN (30%, 0.035% TFA)
  5. customThe collected fractions were stripped to dryness via rotary evaporation

Sources & evidence

ORD record
ord-b11609d8e17648c7b454164c3b24d5f2
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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