Ammonia → HCID 66869037, compound

HRID 1992656Notes

Reaction equation

HRID 1992656 reaction equation
C(O[C:6](=[O:25])[CH2:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=[C:10]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[CH:9]=1)(C)(C)C.C(C1NC=CN=1)(C1[NH:29]C=CN=1)=O.N>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:24][N:21]1[CH2:20][CH2:19][N:18]([C:10]2[CH:9]=[C:8]([CH2:7][C:6]([NH2:29])=[O:25])[C:13]([C:14]([F:16])([F:15])[F:17])=[CH:12][N:11]=2)[CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 66869519HCID 66869519, compound

Product 1

HCID 66869037HCID 66869037, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[2-(4-Methyl-piperazin-1-yl)-5-trifluoromethyl-pyridin-4-yl]-acetic acid tert-butyl ester (475 mg, 1.32 mmol) is dissolved in a mixture of TFA and CH2Cl2 (10 ml/10 ml) and stirred at RT. After 1.5 h at RT, TLC analysis indicated complete conversion of starting material. The solvent is removed by rotary evaporation, and replaced by dry DMF (5 ml). Under an atmosphere of argon, carbonyl diimidazole (236 mg, 1.46 mmol) is added. After 3 h at RT, TLC analysis indicated complete conversion of the carboxylic acid. An aqueous solution of ammonia (25%, 20 ml) is added at RT. After 15 minutes at RT, solvents are removed under high vacuum. The residue is dissolved in CH2Cl2/MeOH (9:1) and purified by FCC (CH2Cl2/MeOH, slow gradient from 90:10 to 40:60) to yield the title compound. 1H NMR (d6-DMSO, 400 MHz): δ 2.69 (s, 3H), 2.93-3.18 (m, broad, 4H), 3.54 (s, 2H), 3.59-3.98 (m, broad, 4H), 6.95 (s, 1H), 7.02 (s, broad, 1H), 7.47 (s, broad, 1H), 8.45 (s, 1H). ES+−MS: 303.2 [M+H]+.

Workup

  1. customThe solvent is removed by rotary evaporation
  2. waitAfter 3 h at RT
  3. waitAfter 15 minutes at RT
  4. customsolvents are removed under high vacuum
  5. dissolutionThe residue is dissolved in CH2Cl2/MeOH (9:1)
  6. custompurified by FCC (CH2Cl2/MeOH, slow gradient from 90:10 to 40:60)

Sources & evidence

ORD record
ord-3ba627c9360d49de88b123f4b5a33245
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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