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Diisopropylethylamine → HCID 68540874, compound

HRID 1993698
Notes
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Reaction equation

HRID 1993698 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)C[O:25][C:26](=O)[NH:27][C:28]1[N:29]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)[N:30]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:32]=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([NH:21][C:26]([NH:27][C:28]3[N:29]([C:37]4[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=4)[N:30]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:32]=3)=[O:25])[CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 68538138HCID 68538138, compound

Product 1

HCID 68540874HCID 68540874, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a solution of 4-(4-amino-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (Preparation 20, 1 g, 3.41 mmol), (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (Preparation 38, 1.38 g, 3.41 mmol), and diisopropylethylamine (1.2 mL, 6.82 mmol) in DMSO (15 mL) at 60° C. for 5 d. Cool the resulting mixture to room temperature and partition between water and ethyl acetate using saturated aq. sodium chloride solution to aid phase separation. Extract the aqueous layer with ethyl acetate, wash the combined organic layers twice with water, dry over sodium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with a gradient of ethyl acetate in dichloromethane to give 877 mg (43% yield) of 4-{4-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-yloxy}-piperidine-1-carboxylic acid tert-butyl ester. LCMS ES+(m/z) 549 [M+H].

Workup

  1. custompartition between water and ethyl acetate using saturated aq. sodium chloride solution
  2. customphase separation
  3. extractionExtract the aqueous layer with ethyl acetate
  4. washwash the combined organic layers twice with water
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate under reduced pressure
  7. washSubject residue to silica gel chromatography eluting with a gradient of ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-99f5589bfa104df185e38a02a189de3f
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07652015B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes