HCID 86651928, compound → HCID 136403437, compound

HRID 1685133Notes

Reaction equation

HRID 1685133 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([NH:50]CC3C=CC(OC)=CC=3OC)=[C:11]([NH:15][C:16]([C:18]3[N:22]([CH3:23])[N:21]=[C:20]([C:24]4[CH:29]=[CH:28][C:27]([C:30]5[CH:31]=[CH:32][C:33]([C:36]([NH:38][CH3:39])=[O:37])=[N:34][CH:35]=5)=[CH:26][CH:25]=4)[C:19]=3[O:40]CC3C=CC(OC)=CC=3)=O)[CH:12]=2)[CH2:7]1>C(O)(=O)C>[OH:40][C:19]1[C:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[CH:32][C:33]([C:36]([NH:38][CH3:39])=[O:37])=[N:34][CH:35]=3)=[CH:26][CH:25]=2)=[N:21][N:22]([CH3:23])[C:18]=1[C:16]1[NH:50][C:10]2=[CH:9][C:8]3[CH2:7][NH:6][CH2:14][C:13]=3[CH:12]=[C:11]2[N:15]=1

Participants

3

Reactant 1

HCID 86651928HCID 86651928, compound

Product 1

HCID 136403437HCID 136403437, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 5-(4-(5-(2-(2,4-dimethoxybenzyl)-6-(2,4-dimethoxybenzylamino)isoindolin-5-ylcarbamoyl)-4-(4-methoxybenzyloxy)-1-methyl-1H-pyrazol-3-yl)phenyl)-N-methylpicolinamide T-14 (410 mg, 0.45 mmol) in acetic acid (4 mL) was heated in a microwave reactor at 150° C. for 50 minutes. Solvent was evaporated under reduced pressure and trifluoroacetic acid (4 mL) was added. The reaction mixture was heated in microwave reactor at 120° C. for 30 minutes. Solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to afford the desired 5-(4-(4-hydroxy-1-methyl-5-(1,5,6,7-tetrahydroimidazo[4,5-f]isoindol-2-yl)-1H-pyrazol-3-yl)phenyl)-N-methylpicolinamide T-15 (143 mg, 0.31 mmol).

Workup

  1. customSolvent was evaporated under reduced pressure and trifluoroacetic acid (4 mL)
  2. additionwas added
  3. customSolvent was evaporated under reduced pressure
  4. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-09b48c44420743d296b29842b2a95344
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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