Acetic Acid → tert-Butyl {2-[(4-{1-[(1,5-dimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzoyl)amino]phenyl}carbamate

HRID 222410Notes

Reaction equation

HRID 222410 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH:8]=O)[CH:4]=[N:3]1.[NH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:38]=[CH:37][C:19]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH2:8][N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:38]=[CH:37][C:19]([C:20]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:21])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:4]=[N:3]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5796431,5-dimethyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59830875Tert-butyl 2-[(4-piperidin-4-ylbenzoyl)amino]phenylcarbamate

Product 1

HCID 59830880tert-Butyl {2-[(4-{1-[(1,5-dimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzoyl)amino]phenyl}carbamateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,5-Dimethyl-1H-pyrazole-4-carbaldehyde (114 mg, 0.92 mmol) was added to a solution of tert-butyl 2-[(4-piperidin-4-ylbenzoyl)amino]phenylcarbamate (289 mg, 0.73 mmol) in dichloromethane (6 ml) followed by acetic acid (50 μl, 0.87 mmol). The reaction mixture was allowed to stir under nitrogen for 2.5 hours. Sodium triacetoxyborohydride (233 mg, 1.10 mmol) was added and the reaction mixture allowed to stir, at ambient temperature, for 18 hours (overnight). Saturated aqueous sodium bicarbonate solution (10 ml) was then added to the reaction and allowed to stir for 15 minutes. The organic phase was separated and the aqueous phase re-extracted with dichloromethane (10 ml). The combined organics were washed with water, dried over magnesium sulphate and evaporated to dryness to afford the product as a colourless gum (308 mg, 84%), which was used without further purification; Mass Spectrum: M+H+504.

Workup

  1. stirringto stir, at ambient temperature, for 18 hours (overnight)
  2. stirringto stir for 15 minutes
  3. customThe organic phase was separated
  4. extractionthe aqueous phase re-extracted with dichloromethane (10 ml)
  5. washThe combined organics were washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-cdca534bab4c44b887943abca852c687
Source dataset
uspto-grants-2012_06
Patent number
US08207202B2

Reaction notes

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