Triethylamine → methyl (S)-3-chloro-4-[2-[4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate

HRID 354491Notes

Reaction equation

HRID 354491 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C2C(F)=C(F)C(F)=C(F)C=2F)=O)=[CH:13][CH:12]=1.[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C@@H:46]([NH2:48])[CH3:47])[C:37]([O:39][CH3:40])=[O:38].CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C@@H:46]([NH:48][C:18](=[O:20])[CH2:17][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[O:32])=[CH:16][CH:15]=1)[CH3:47])[C:37]([O:39][CH3:40])=[O:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23512272pentafluorophenyl 4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 86587793methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate

Product 1

HCID 86587792methyl (S)-3-chloro-4-[2-[4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoateYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of pentafluorophenyl 4-[N′-(2-methylphenyl)ureido]phenylacetate (508 mg, 1.13 mmol), methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate (275 mg, 1.13 mmol) and Et3N (0.240 mL, 1.72 mmol) in DMF (10 mL) was stirred at room temp overnight. The mixture was diluted with EtOAc, and the solution was washed with 0.5 N HCl, sat. NaHCO3, brine, dried over Na2SO4, and evaporated. The residue was recrystallized from MeOH—CHCl3-n-hexane to give 240 mg (42%) methyl (S)-3-chloro-4-[2-[4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate as a white crystalline powder. 1H-NMR (DMSO-d6) δ1.21 (d, 3H, J=6.4 Hz), 2.25 (s, 3 H), 3.33 (s, 2 H), 3.82 (s, 3 H), 4.04-4.14 (m, 3H), 6.90-6.94 (m, 1H), 7.11-7.16 (m, 4H), 7.29-7.38 (m, 3H), 7.83-7.94 (m, 3H), 8.13-8.17 (m, 2H), 9.34 (s, 1 H); MS(FAB) m/z 510 (M30).

Workup

  1. washthe solution was washed with 0.5 N HCl, sat. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was recrystallized from MeOH—CHCl3-n-hexane

Sources & evidence

ORD record
ord-b6d759512e9747b5aac11493f0a3174f
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

Loading…