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

HRID 711570Notes

Reaction equation

HRID 711570 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]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([NH:20][CH3:21])=[O:19])[N:10]=[C:9]([C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)[C:8]=2[C:7]1=[O:32]>C(O)(C(F)(F)F)=O>[F:15][C:12]1[C:13]2[CH2:14][NH:6][C:7](=[O:32])[C:8]=2[C:9]([C:26]2[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=2)=[N:10][C:11]=1[NH:16][C@H:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([NH:20][CH3:21])=[O:19]

Participants

3

Reactant 1

HCID 67238387(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)-N,4-dimethylpentanamide

Product 1

HCID 53251341(R)-2-(7-Fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide

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)-N,4-dimethylpentanamide (38 mg, 0.072 mmol) in TFA (5 mL) was heated to 65° C. for 4 h. After removal of the solvent, the residue was diluted in MeOH (2 mL) and was purified by preparative HPLC eluting with water (0.05% TFA) and ACN (25-30%, gradient, 0.035% TFA). The collected fractions were stripped to dryness to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 0.84-0.93 (m, 6H), 1.63-1.81 (m, 2H), 2.57 (d, J=4.39 Hz, 3H), 3.88 (s, 3H), 4.04-4.19 (m, 2H), 4.36 (s, 2H), 6.99 (d, J=7.32 Hz, 1H), 7.61-7.76 (m, 1H), 7.93 (d, J=4.39 Hz, 1H), 8.30 (s, 1H), 8.83 (s, 1H). [M+H] calc'd for C18H23FN6O2, 375. found, 375.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was diluted in MeOH (2 mL)
  3. customwas purified by preparative HPLC
  4. washeluting with water (0.05% TFA) and ACN (25-30%, gradient, 0.035% TFA)

Sources & evidence

ORD record
ord-d049de2006064850b07ecdf8ee14d5f4
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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