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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-methoxymethoxy-4-methyl-N-(1-methyl-1-phenylethyl)benzamide

HRID 21274
Notes
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Reaction equation

HRID 21274 reaction equation
CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:23]([NH2:32])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:25])[CH3:24].[CH3:33][O:34][CH2:35][O:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][C:45]=1[CH3:46])[C:40](O)=[O:41]>CN(C=O)C>[CH3:33][O:34][CH2:35][O:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][C:45]=1[CH3:46])[C:40]([NH:32][C:23]([CH3:25])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:24])=[O:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 596497153-(Methoxymethoxy)-4-methylbenzoic acid

Product 1

HCID 684929793-methoxymethoxy-4-methyl-N-(1-methyl-1-phenylethyl)benzamideYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Example 137, 3-methoxymethoxy-4-methylbenzoic acid (2.69 g) was dissolved in DMF (53 mL), and the solution was treated with EDCI (5.04 g, 26.3 mmol), HOBT monohydrate (2.01 g, 13.1 mmol) and cumylamine (3.80 mL, 26.4 mmol), followed by purification by slurry using hexane to obtain 3-methoxymethoxy-4-methyl-N-(1-methyl-1-phenylethyl)benzamide (3.42 g, yield 83%, 2 steps).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-f2c8862367344837b0cf1963da893a4f
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745641B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes