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Diisopropylethylamine → tert-Butyl 5-((1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

HRID 928445
Notes
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Reaction equation

HRID 928445 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8]CC)=O)[CH:3]=[N:2]1.[CH3:11]CN(C(C)C)C(C)C.[NH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[N:26][C:27]=1[CH3:28].CCCP(=O)=O>CN(C=O)C.C(OCC)(=O)C.O>[NH:2]1[CH:3]=[C:4]([C:6]([NH:20][CH2:21][C:22]2[C:23]([CH3:11])=[CH:24][C:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[N:26][C:27]=2[CH3:28])=[O:8])[CH:5]=[N:1]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 10681361tert-Butyl 5-(aminomethyl)-6-methylpyridin-2-ylcarbamateHCID 16167369Propylphosphoric anhydride

Product 1

HCID 58081315tert-Butyl 5-((1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The starting material ethyl pyrazole-4-carboxylate was saponified in analogy to Example 157, Step a), To a solution of the free acid (1 g, 5.86 mmol) in DMF (40 ml) were added DIPEA (4.10 ml, 23.46 mmol) and tert-butyl (5-(aminomethyl)-6-methylpyridin-2-yl)carbamate (1.531 g, 6.45 mmol). At 0° C., propylphosphonic anhydride (50% in DMF, 3.42 ml, 5.86 mmol) was added dropwise. Reaction mixture was stirred for 30 min at 0° C., then diluted with ethyl acetate and water. Phases were separated and organic layer was washed with NaHCO3 sat. solution and brine. Organic layer was dried over sodium sulfate, filtered and evaporated to afford the crude material, which was purified by silicagel chromatography (DCM/MeOH from 100/0 to 9/1 in 30 min) to afford the title compound. HPLC (Method G) Rt=1.209 min, MS (Method V) [M+H]+=332.3.

Workup

  1. customReaction mixture
  2. customPhases were separated
  3. washorganic layer was washed with NaHCO3 sat. solution and brine
  4. dry with materialOrganic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford the crude material, which
  8. customwas purified by silicagel chromatography (DCM/MeOH from 100/0 to 9/1 in 30 min)

Sources & evidence

ORD record
ord-489ca6eaf2244d638c85f9d2a1f6c8c9
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290485B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes