1,2-Dichloroethane → methyl 4-[[1-[4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate

HRID 354494Notes

Reaction equation

HRID 354494 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([CH3:17])([O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)[CH3:5].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35](O)=[O:36])=[CH:30][C:29]=1[O:38][CH3:39].C(Cl)CCl.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35]([CH2:1][NH:2][CH2:3][C:4]([CH3:17])([O:6][C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[CH3:5])=[O:36])=[CH:30][C:29]=1[O:38][CH3:39]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 23511825HCID 23511825, compoundHCID 69333050Methyl 4-(1-methylamino-2-methyl-2-propoxy)benzoate

Product 1

HCID 69334761methyl 4-[[1-[4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoateYield 44.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of methyl 4-(1-methylamino-2-methyl-2-propoxy)benzoate (200 mg, 0.84 mmol), 4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetic acid (268 mg, 0.84 mmol), 4-DMAP (125 mg, 1.0 mmol) in DMF (5 mL) was added EDC (220 mg, 1.14 mmol) at ambient temp. The resulting mixture was stirred for a further 10 hr at ambient temp. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated. The residual gum was triturated with CH2Cl2 and Et2O to give 200 mg (44.1%) methyl 4-[[1-[4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate as a crystalline material. 1H-NMR (CDCl3) δ1.36 and 1.31 (each s, 6H), 3.24-3.88 (series of s, 13 H), 6.65-8.20 (series of m, 14H).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residual gum was triturated with CH2Cl2 and Et2O

Sources & evidence

ORD record
ord-a2935f98208d4f0290ee014926308275
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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