Dimethylamine → HCID 18758349, compound

HRID 2244536Notes

Reaction equation

HRID 2244536 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8](=[O:32])[N:9]([CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=1)[CH2:17][C:18]([OH:20])=O)[C:10]2=[O:15])=[O:4].[C:33](N1C=CN=C1)([N:35]1C=CN=[CH:36]1)=O.CNC.O>O1CCCC1.C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8](=[O:32])[N:9]([CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=1)[CH2:17][C:18]([N:35]([CH3:36])[CH3:33])=[O:20])[C:10]2=[O:15])=[O:4]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 18758341HCID 18758341, compound

Product 1

HCID 18758349HCID 18758349, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[4-(2-chloroacetylamino)-1,3-dioxoisoindolin-2-yl]-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (1.0 g, 2.2 mmol) and carbonyldiimidazole (367 mg, 2.26 mmol) in tetrahydrofuran (7 mL) was stirred at room temperature for 1 h. To the mixture was added dimethylamine in tetrahydrofuran (1.3 mL, 2 N, 2.6 mmol) and the mixture was stirred for 2 h. Water (60 mL) and methylene chloride (50 mL) were then added to mixture. The aqueous layer was separated and was extracted with ethyl acetate (50 mL). The combined organic layers was washed with brine/hydrogen chloride 1N (1:1, 50 mL), and dried over magnesium sulfate. The solvent was removed in vacuo to give 3-[4-(2-chloroacetylamino)-1,3-dioxoisoindolin-2-yl]-3-(3-ethoxy-4-methoxyphenyl)-N,N-dimethylpropanamide as a yellow solid (1.1 g, 100% yield), which was used in the next step without further purification.

Workup

  1. customThe aqueous layer was separated
  2. extractionwas extracted with ethyl acetate (50 mL)
  3. washThe combined organic layers was washed with brine/hydrogen chloride 1N (1:1, 50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-920cf64b2dce4ecdbd4d1f5f0f480182
Source dataset
uspto-grants-2010_03
Patent number
US07678825B2

Reaction notes

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