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Hydrochloric Acid → Pyridin-3-ylmethyl (4-{[(4-amino-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}benzyl)carbamate

HRID 913246
Notes
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Reaction equation

HRID 913246 reaction equation
C(OC([NH:8][C:9]1[C:10]([NH:20][C:21]([C:23]2[CH:40]=[CH:39][C:26]([CH2:27][NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[CH:25][CH:24]=2)=[O:22])=[N:11][N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1)=O)(C)(C)C.Cl.O1CCOCC1>C(OCC)(=O)C.CO>[NH2:8][C:9]1[C:10]([NH:20][C:21]([C:23]2[CH:40]=[CH:39][C:26]([CH2:27][NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[CH:25][CH:24]=2)=[O:22])=[N:11][N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86636503HCID 86636503, compound

Product 1

HCID 16066810Pyridin-3-ylmethyl (4-{[(4-amino-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}benzyl)carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

A solution of pyridin-3-ylmethyl {4-[({4-[(tert-butoxycarbonyl)amino]-1-phenyl-1H-pyrazol-3-yl}amino)carbonyl]benzyl}carbamate (0.075 g, 0.14 mmol) in ethyl acetate (2 mL) and methanol (1 mL) was treated with 4M HCl in dioxane (3.11 mL, 12.4 mmol) and stirred at ambient temperature for 12 hours. The reaction was evaporated in vacuo and purified by flash column chromatography (0-5% methanol/methylene chloride w/0.1% ammonia) to give the title compound as an off-white solid. 1H NMR (CD3OD) δ 8.58 (s, 1H), 8.48 (m, 1H), 7.96 (d, J=8.22 Hz, 2H), 7.87 (d, J=8.22 Hz, 1H), 7.79 (s, 1H), 7.65 (d, J=8.22 Hz, 2H), 7.42 (m, 5H), 7.22 (t, J=7.30 Hz, 1H), 5.18 (s, 2H), 4.38 (s, 2H).

Workup

  1. customThe reaction was evaporated in vacuo
  2. custompurified by flash column chromatography (0-5% methanol/methylene chloride w/0.1% ammonia)

Sources & evidence

ORD record
ord-fa286d4e5f17483ca4b73076765b10a4
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026260B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes