4-Methyloxybenzyl chloride → HCID 178440426, compound

HRID 921560Notes

Reaction equation

HRID 921560 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](CC3C=CC(OC)=CC=3)[N:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:3]=12.IC1C=CN=C2NN=C(C(C)C)C=12.COC1C=CC(CCl)=CC=1.Cl.[CH3:47][N:48]1[CH:52]=[C:51]([C:53]2[N:54]=[CH:55][NH:56][CH:57]=2)[CH:50]=[N:49]1>>[CH:11]([C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[N:56]2[CH:57]=[C:53]([C:51]3[CH:50]=[N:49][N:48]([CH3:47])[CH:52]=3)[N:54]=[CH:55]2)[NH:8][N:9]=1)([CH3:12])[CH3:13]

Participants

5

Reactant 4

HCID 699934-Methyloxybenzyl chlorideHCID 675027634-iodo-3-isopropyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine2×HCID 178440425HCID 178440425, compoundHCID 178478913HCID 178478913, compound

Product 1

HCID 178440426HCID 178440426, compoundYield 63%

Procedure

According to Example 97(1), 4-iodo-3-isopropyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine was prepared using compound (100a) (15.5 g) instead of compound (40d) and using 4-methoxybenzyl chloride instead of {2-(chloromethoxy)ethyl}silane and was used in the subsequent reaction without being purified. According to Example 97(2), 3-isopropyl-1-(4-methoxybenzyl)-4-{4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl}-1H-pyrazolo[3,4-b]pyridine was prepared using 4-iodo-3-isopropyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine instead of compound (97a) and using 4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazole hydrochloride instead of 4-phenyl-1H-imidazole and was used in the subsequent reaction without being purified. This 3-isopropyl-1-(4-methoxybenzyl)-4-{4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl}-1H-pyrazolo[3,4-b]pyridine was dissolved in trifluoroacetic acid (60 mL) and anisole (19 mL), followed by reflux for 5 hr. The reaction solution was concentrated and then diluted with acetonitrile, and saturated sodium bicarbonate water was added thereto. The precipitate was collected by filtration and was dried under reduced pressure to obtain compound (100b) (12.3 g, the third stage yield: 63%) as a white solid.

Workup

  1. customwas prepared
  2. customwas used in the subsequent reaction
  3. customwithout being purified
  4. customwas prepared
  5. customwas used in the subsequent reaction
  6. customwithout being purified
  7. dissolutionThis 3-isopropyl-1-(4-methoxybenzyl)-4-{4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl}-1H-pyrazolo[3,4-b]pyridine was dissolved in trifluoroacetic acid (60 mL)
  8. temperatureby reflux for 5 hr
  9. concentrationThe reaction solution was concentrated
  10. additiondiluted with acetonitrile, and saturated sodium bicarbonate water
  11. additionwas added
  12. filtrationThe precipitate was collected by filtration
  13. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-aa07097232eb4205a1b1d427b91c1f56
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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