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Potassium Carbonate → [2-[(3,5-Dimethoxy-4-methyl-benzoylamino)-methyl]-5-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenylamino]-acetic acid benzyl ester

HRID 1296748
Notes
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Reaction equation

HRID 1296748 reaction equation
[NH2:1][C:2]1[CH:22]=[C:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1.Br[CH2:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][NH:1][C:2]1[CH:22]=[C:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 69491883N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide

Product 1

HCID 69491566[2-[(3,5-Dimethoxy-4-methyl-benzoylamino)-methyl]-5-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenylamino]-acetic acid benzyl esterYield 48%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of compound 1g (382 mg, 1.0 mmol), benzyl 2-bromoacetate (0.224 mL, 1.4 mmol), and potassium carbonate (276 mg, 2.0 mmol) in DMF (3 mL) was sealed in a pressure tube and heated at 80° C. for 5 h and at rt for two days. The reaction mixture was diluted with water, and the resulting solid precipitate was recovered by filtration and washed with MeOH and hexane to give compound 14a (252 mg, 48%) as a yellow solid. ESI-MS m/e 531.3 (M+1).

Workup

  1. customwas sealed in a pressure tube
  2. filtrationthe resulting solid precipitate was recovered by filtration
  3. washwashed with MeOH and hexane

Sources & evidence

ORD record
ord-1b40b136d8d0454ab17fd4aab0c7217a
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07247654B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes