Methyl 2-t-butoxycarbonylamino-4-[4-[4-(4-pyridyl)-piperazin-1-yl]phenoxy]butyrat → Methyl 2-amino-4-[4-[4-(4-pyridyl)piperazin-1-yl]-phenoxy]butyrate

HRID 2249Notes

Reaction equation

HRID 2249 reaction equation
C(OC([NH:8][CH:9]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][CH:9]([CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:24][CH2:25][N:26]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[CH2:27][CH2:28]2)=[CH:21][CH:22]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

3

Reactant 1

HCID 18918622Methyl 2-t-butoxycarbonylamino-4-[4-[4-(4-pyridyl)-piperazin-1-yl]phenoxy]butyrat

Product 1

HCID 18918214Methyl 2-amino-4-[4-[4-(4-pyridyl)piperazin-1-yl]-phenoxy]butyrateYield 74.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The compound of Example 140 (0.96 g) in TFA (10 ml) was kept at room temperature for 2 hours. The solution was evaporated and the residue dissolved in water (15 ml) and the solution basified with sodium carbonate. The mixture was extracted three times with dichloromethane. Evaporation of the combined extracts gave the title compound (0.56 g); m.p. 125°-127° C.; NMR(d6DMSO) δ 8.2(2H,d), 6.92(6H,m), 4.0(2H,m), 3.64(3H,s), 3.46(4H,t), 3.15(4H,t), 2.04(2H,m), 1.84(1H, m); m/e 371(M+H)+. Calculated for C20H26N4 O3. 0.75 H2O: C, 62.5; H, 7.17; N, 14.6. Found: C, 62.8; H, 6.8; N, 14.3%.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue dissolved in water (15 ml)
  3. extractionThe mixture was extracted three times with dichloromethane
  4. customEvaporation of the combined extracts

Sources & evidence

ORD record
ord-bc4c5bfd0a2540ebba7d4dbbdd3411b3
Source dataset
uspto-grants-1998_03
Patent number
US05728701

Reaction notes

Loading…