Hydrochloric Acid → 2-(6-(1H-Indol-4-yl)-1H-indazol-4-yl)-5-((4-isopropylpiperazin-1-yl)methyl)oxazole hydrochloride

HRID 2039713Notes

Reaction equation

HRID 2039713 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][NH:16]4)=[C:12]([C:19]4[O:20][C:21]([CH2:24][N:25]5[CH2:30][CH2:29][N:28]([CH:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]5)=[CH:22][N:23]=4)[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[ClH:34].C(OCC)C>O1CCCC1>[ClH:34].[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][NH:16]4)=[C:12]([C:19]4[O:20][C:21]([CH2:24][N:25]5[CH2:26][CH2:27][N:28]([CH:31]([CH3:33])[CH3:32])[CH2:29][CH2:30]5)=[CH:22][N:23]=4)[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 49784002Nemiralisib

Product 1

HCID 497840842-(6-(1H-Indol-4-yl)-1H-indazol-4-yl)-5-((4-isopropylpiperazin-1-yl)methyl)oxazole hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1H-indazole in tetrahydrofuran (THF) (7.5 mL) was heated to 60° C. under nitrogen. 2M hydrochloric acid in diethyl ether (0.567 mL, 1.135 mmol) and tetrahydrofuran (THF) (0.5 mL) were mixed and added via a dropping funnel. The solution was stirred at 60° C. for 30 mins before being slowly cooled to RT. After stirring at RT for a further 30mins the solid was filtered off, then recombined with the liquors and evaporated to dryness. THF (10 mL) was added and the slurry was cycled from RT to reflux 3 times (30 mins hold at higher/low temp). The slurry was stirred at RT for one hour then filtered under vacuum and the resultant solid dried in a vacuum oven at 50° C. overnight to give the title compound as a an off-white solid (322 mg).

Workup

  1. additionadded via a dropping funnel
  2. temperaturebefore being slowly cooled to RT
  3. stirringAfter stirring at RT for a further 30mins the solid
  4. filtrationwas filtered off
  5. customevaporated to dryness
  6. additionTHF (10 mL) was added
  7. customwas cycled from RT
  8. temperatureto reflux 3 times (30 mins hold at higher/low temp)
  9. stirringThe slurry was stirred at RT for one hour
  10. filtrationthen filtered under vacuum
  11. customthe resultant solid dried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-8ac4bfe601ba4995a046a28152a42af4
Source dataset
uspto-grants-2013_11
Patent number
US08580797B2

Reaction notes

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