HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

1,2-Dichloroethane → methyl 4-[[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-methyl-2-pyrrolidinyl]methoxy]-3-nitrobenzoate

HRID 350381
Notes
Print preview

Reaction equation

HRID 350381 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1([CH3:21])[CH2:20][CH2:19][CH2:18][NH:17]1)[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:41][C:42](O)=[O:43])[CH:27]=[CH:28][C:29]=1[NH:30][C:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:40])=[O:32].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:41][C:42]([N:17]2[CH2:18][CH2:19][CH2:20][C:16]2([CH2:15][O:14][C:13]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH3:21])=[O:43])[CH:27]=[CH:28][C:29]=1[NH:30][C:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:40])=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23512125Methyl 3-nitro4-(2-methyl-2-pyrrolidinylmethoxy)benzoate

Product 1

HCID 23512434methyl 4-[[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-methyl-2-pyrrolidinyl]methoxy]-3-nitrobenzoate
Yield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-nitro4-(2-methyl-2-pyrrolidinylmethoxy)benzoate (0.188 g, 0.920 mmol), 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (0.289 g, 0.920 mmol), HOBt (0.149 g, 1.10 mmol), DMAP. (11.2 mg, 0.0920 mmol) and EDC (0.211 g, 1.10 mmol) in DMF (5 mL) was stirred for 14 hr at room temp. EtOAC was added to the mixture and the solution was washed successively with 0.5 N HCl, sat. NaHCO3, and brine. The organic layer was dried over Na2SO4 and evaporated in vacuo to afford 0.489 g (q.y.) methyl 4-[[1-[3-methoxy4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-methyl-2-pyrrolidinyl]methoxy]-3-nitrobenzoate as a yellow crystalline material. 1H-NMR (CDCl3) δ 1.26 (d, J=5.9 Hz), 1.85–4.50 (m, 10H), 2.30 (s, 3H), 3.67 (s, 2H), 3.92 (s, 3H), 6.36 (s, 2H), 6.75–7.52 (m, 7H), 8.02 (d, J=7.8 Hz, 1H), 8.15 (d, J=8.8 Hz, 1H), 8.47 (s, 1H).

Workup

  1. additionEtOAC was added to the mixture
  2. washthe solution was washed successively with 0.5 N HCl, sat. NaHCO3, and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-1dd0a9687a034d2caa8dcde2c0439a67
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179819B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes