Ammonia → 2-[5-Methyl-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetamide

HRID 1992645ノート

反応式

HRID 1992645 の反応式
C([O:5][C:6](=O)[CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][N:11]=[C:10]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:9]=1)(C)(C)C.C(C1NC=CN=1)(C1[NH:26]C=CN=1)=O.N>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:14][C:13]1[C:8]([CH2:7][C:6]([NH2:26])=[O:5])=[CH:9][C:10]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[N:11][CH:12]=1

参加物

6

反応物 3

HCID 222AmmoniaHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 66869033[5-Methyl-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetic acid tert-butyl ester

生成物 1

HCID 668699142-[5-Methyl-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

[5-Methyl-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetic acid tert-butyl ester (320 mg, 1.05 mmol) is dissolved in a mixture of TFA and CH2Cl2 (10 ml/10 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 (187 mg, 1.16 mmol) is added. After 30 minutes at RT, TLC analysis indicated complete conversion of the carboxylic acid. An aqueous solution of ammonia (25%, 16 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 (d6-DMSO, 400 MHz): δ 2.07 (s, 3H), 2.38 (s, 3H), 2.64 (s, broad, 4H), 3.34 (s, 2H), 3.46 (s, broad, 4H), 6.72 (s, 1H), 6.95 (s, broad, 1H), 7.44 (s, broad, 1H), 7.87 (s, 1H). ES+−MS: 249.3 [M+H]+, ES−−MS: 247.3 [M−H]−.

後処理

  1. customThe solvent is removed by rotary evaporation
  2. waitAfter 30 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)

出典と根拠

ORDレコード
ord-ee3bf67ea38049e1ba9e53c9f237b981
出典データセット
uspto-grants-2010_01
特許番号
US07648989B2

反応ノート

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