Ammonia → HCID 66869527, compound

HRID 1992642Notes

Reaction equation

HRID 1992642 reaction equation
C([O:5][C:6](=O)[CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:9]=1)(C)(C)C.C(C1NC=CN=1)(C1[NH:25]C=CN=1)=O.N>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:20][N:17]1[CH2:18][CH2:19][N:14]([C:10]2[CH:9]=[C:8]([CH2:7][C:6]([NH2:25])=[O:5])[CH:13]=[CH:12][N:11]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 66869321HCID 66869321, compound

Product 1

HCID 66869527HCID 66869527, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[2-(4-Methyl-piperazin-1-yl)-pyridin-4-yl]-acetic acid tert-butyl ester (95 mg, 0.33 mmol) is dissolved in a mixture of TFA and CH2Cl2 (5 ml/5 ml) and stirred at RT. After 1 h at RT, TLC analysis indicated complete conversion of starting material. The solvent is removed by rotary evaporation, and replaced by dry DMF (1.5 ml). Under an atmosphere of argon, carbonyl diimidazole (58 mg, 0.36 mmol) is added. After 20 minutes at RT, TLC analysis indicated complete conversion of the carboxylic acid. An aqueous solution of ammonia (25%, 6 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 95:5 to 40:60) to yield the title compound. 1H NMR (d4-MeOD, 400 MHz): δ 2.35 (s, 3H), 2.56 (m, 4H), 3.46 (s, 2H), 3.54 (m, 4H), 6.66 (d, J=6 Hz, 1H), 6.78 (s, 1H), 8.02 (d, J=6 Hz, 1H). ES+−MS: 235.3 [M+H]+.

Workup

  1. customThe solvent is removed by rotary evaporation
  2. waitAfter 20 minutes 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 95:5 to 40:60)

Sources & evidence

ORD record
ord-79b821f50f9d4ee684efc60eadcb8088
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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