Hydrochloric Acid → HCID 54586652, compound

HRID 1712970Notes

Reaction equation

HRID 1712970 reaction equation
COC1C=CC(C[O:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[CH2:20][CH:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[OH:27])[N:18]([C:28]([C:30]4[S:31][C:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=5)=[CH:33][CH:34]=4)=[O:29])[N:17]=3)[CH:13]=[N:14][CH:15]=2)=CC=1.Cl>CO>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH2:20][CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])[N:18]([C:28]([C:30]3[S:31][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:33][CH:34]=3)=[O:29])[N:17]=2)[CH:13]=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59463396HCID 59463396, compound

Product 1

HCID 54586652HCID 54586652, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 2-{3-(5-{[(4-methoxybenzyl)oxy]methyl}pyridin-3-yl)-1-[(5-pyridin-2-yl-2-thienyl)carbonyl]-4,5-dihydro-1H-pyrazol-5-yl}phenol (0.070 g, 0.12 mmol) in MeOH (6 mL) was added HCl. The reaction mixture was allowed to stir at 65° C. for 6 h and then at rt overnight. Reaction was incomplete, so the mixture was allowed to stir at 65° C. for an additional 10 h and then cooled to rt and concentrated. The residue was purified by column chromatography to give 2-{3-[5-(hydroxymethyl)pyridin-3-yl]-1-[(5-pyridin-2-yl-2-thienyl)carbonyl]-4,5-dihydro-1H-pyrazol-5-yl}phenol (I-273). LCMS: (FA) ES+ 457.4, ES-455.5.

Workup

  1. customat rt
  2. customovernight
  3. customReaction
  4. stirringto stir at 65° C. for an additional 10 h
  5. temperaturecooled to rt
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9c8ae023407d477987225c7b52c37c83
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

Loading…