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

HRID 2092836Notes

Reaction equation

HRID 2092836 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[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=3)[C:8]=2[C:7]1=[O:31]>C(O)(C(F)(F)F)=O>[F:15][C:12]1[C:13]2[CH2:14][NH:6][C:7](=[O:31])[C:8]=2[C:9]([C:25]2[CH:26]=[N:27][N:28]([CH3:30])[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 58317690(R)-2-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide

Product 1

HCID 53250520(R)-2-(7-Fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamideYield 46%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-2-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide (39.8 mg, 0.078 mmol) in TFA (5 mL) was heated at 60° C. for 2 h. After removal of solvent, the residue was diluted in MeOH (2 mL) and was purified by preparative HPLC. The fractions were collected and the solvent stripped to dryness via rotary evaporation to yield the title compound (12.8 mg, 46%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.82-1.00 (m, 6H), 1.45-1.60 (m, 1H), 1.67-1.83 (m, 2H), 3.87 (s, 3H), 4.36 (s, 2H), 4.50-4.64 (m, 1H), 6.88-7.02 (m, 2H), 7.44 (s, 1H), 8.28 (s, 2H), 8.83 (s, 1H). [M+H] calc'd for C17H21FN6O2, 361. found, 361.

Workup

  1. customAfter removal of solvent
  2. additionthe residue was diluted in MeOH (2 mL)
  3. customwas purified by preparative HPLC
  4. customThe fractions were collected
  5. customthe solvent stripped to dryness via rotary evaporation

Sources & evidence

ORD record
ord-0e1578204ce34f2292c09f2c52414b55
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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