Triethylamine → HCID 66958885, compound

HRID 1984419Notes

Reaction equation

HRID 1984419 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH2:14][C:15]([C:17]1[CH:21]=[C:20]([CH2:22][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:25])[CH3:24])[N:19]([CH2:34][CH2:35][CH3:36])[N:18]=1)=O.C(N(CC)CC)C>ClCCl>[C:15]([C:17]1[CH:21]=[C:20]([CH2:22][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:25])[CH3:24])[N:19]([CH2:34][CH2:35][CH3:36])[N:18]=1)#[N:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 66959012HCID 66959012, compound

Product 1

HCID 66958885HCID 66958885, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluoroacetic anhydride (3.93 mL, 27.8 mmol) in dichloromethane (51 mL) was added slowly to a 0° C. solution of tert-butyl 2-[3-(aminocarbonyl)-1-propyl-1H-pyrazol-5-yl]-1,1-dimethylethylcarbamate (8.21 g, 25.3 mmol) and triethylamine (10.6 mL, 75.9 mmol) in dichloromethane (51 mL). After the addition was complete, the cooling bath was removed and the solution was stirred for 90 minutes. The solution was transferred to a separatory funnel and washed with 2 M aqueous sodium carbonate (200 mL). The aqueous layer was extracted twice with chloroform. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield an off white solid that was recrystallized from 10% ethyl acetate in hexanes, isolated by filtration, and dried to yield 6.77 g of tert-butyl 2-(3-cyano-1-propyl-1H-pyrazol-5-yl)-1,1-dimethylethylcarbamate as a white crystals, mp 115-116° C. MS (ESI) m/z 307 (M+H)+; Anal. Calcd for C16H26N4O2: C, 62.72; H, 8.55; N, 18.28. Found: C, 62.61; H, 8.46; N, 18.52.

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. customThe solution was transferred to a separatory funnel
  4. washwashed with 2 M aqueous sodium carbonate (200 mL)
  5. extractionThe aqueous layer was extracted twice with chloroform
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield an off white solid
  10. customthat was recrystallized from 10% ethyl acetate in hexanes
  11. customisolated by filtration
  12. customdried

Sources & evidence

ORD record
ord-162a05b0996348b8aa5a571f181f6e84
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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