Trifluoroacetic acid → 3-(1H-benzo[d]imidazol-2-yl)-5-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

HRID 1959407ノート

反応式

HRID 1959407 の反応式
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:27]2[N:31](C(OC(C)(C)C)=O)[C:30]3[CH:39]=[CH:40][CH:41]=[CH:42][C:29]=3[N:28]=2)=[N:11][C:12]([C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH:20]=2)=[CH:13][N:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:28]1[C:29]2[CH:42]=[CH:41][CH:40]=[CH:39][C:30]=2[N:31]=[C:27]1[C:10]1[C:9]([NH2:8])=[N:14][CH:13]=[C:12]([C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:19][CH:20]=2)[N:11]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 66745113Tert-butyl 2-(3-(bis(tert-butoxycarbonyl)amino)-6-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-yl)-1H-benzo[d]imidazole-1-carboxylate

生成物 1

HCID 667455743-(1H-benzo[d]imidazol-2-yl)-5-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine収率 14.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl 2-(3-(bis(tert-butoxycarbonyl)amino)-6-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-yl)-1H-benzo[d]imidazole-1-carboxylate (100 mg, 0.1495 mmol) in DCM (1 mL) was treated with TFA (1 mL, 12.98 mmol) and allowed to stir at ambient temperature for 40 minutes. The reaction was concentrated in vacuo and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a pale brown solid (8.0 mg, 14% Yield). 1H NMR (400.0 MHz, DMSO) d 2.84 (2H, m), 3.53 (2H, m), 3.94 (2H, m), 6.76-6.90 (3H, m), 7.20-7.69 (6H, m), 7.70-9.39 (4H, m), 12.88 (1H, m) ppm; MS (ES+) 369.02

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were collected
  4. customfreeze-dried

出典と根拠

ORDレコード
ord-9acc32b305194e87b1a50b2148df2df4
出典データセット
uspto-grants-2013_04
特許番号
US08410112B2

反応ノート

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