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Diisopropylethylamine → {5-tert-Butyl-2-[3-(2-hydroxy-ethylsulfanyl)-phenyl]-2H-pyrazol-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 572059
Notes
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Reaction equation

HRID 572059 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].[NH2:10][C:11]1[N:15]([C:16]2[CH:17]=[C:18]([S:22][CH2:23][CH2:24][OH:25])[CH:19]=[CH:20][CH:21]=2)[N:14]=[C:13]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:12]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:7][C:6]([Cl:9])([Cl:8])[CH2:5][O:4][C:2](=[O:3])[NH:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22][CH2:23][CH2:24][OH:25])[CH:17]=2)[N:14]=[C:13]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 866866782-[3-(5-Amino-3-tert-butyl-pyrazol-1-yl)phenylsulfanyl]-ethanol

Product 1

HCID 86686677{5-tert-Butyl-2-[3-(2-hydroxy-ethylsulfanyl)-phenyl]-2H-pyrazol-3-yl}-carbamic acid 2,2,2-trichloro-ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Trichloroethyl chloroformate (0.1 mL, 0.78 mmol) was added to a solution of Intermediate 3b (176 mg, 0.60 mmol) and DIPEA (0.31 mL, 1.81 mmol) in THF (10 mL), and the mixture stirred for 3 h. The mixture was then partitioned between water (15 mL) and EtOAc (3×20 mL), and the combined organic extracts dried (Na2SO4) and concentrated in vacuo. The residue was triturated (cyclohexane) and filtered to give the title compound as a yellow solid (280 mg, 100%). LCMS (Method 1): Rt 3.93 min, m/z 466/468 [MH+]

Workup

  1. customThe mixture was then partitioned between water (15 mL) and EtOAc (3×20 mL)
  2. dry with materialthe combined organic extracts dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated (cyclohexane)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5a8f97a20719493d8dce17173e8408e9
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029373B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes