4-Methylmorpholine → (E)-N-methyl-N-carboxymethyl-4-[2-(1H-indazol-3-yl)vinyl]benzamide

HRID 2075449Notes

Reaction equation

HRID 2075449 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)=[N:2]1.Cl.C([O:24][C:25](=[O:29])[CH2:26][NH:27][CH3:28])C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1>[OH-].[Na+]>[CH3:28][N:27]([CH2:26][C:25]([OH:29])=[O:24])[C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12](/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11437002(E)-4-(2-(1H-indazol-3-yl)vinyl)benzoic acid

Product 1

HCID 23118630(E)-N-methyl-N-carboxymethyl-4-[2-(1H-indazol-3-yl)vinyl]benzamideYield 55%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The product obtained using (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (1.50 g, 5.68 mmol), sarcosine ethyl ester hydrochloride (1.05 g, 6.81 mmol), 1-hydroxybenzotriazole monohydrate (1.31 g, 6.81 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.63 g, 8.52 mmol) and N-methylmorpholine (1.87 mL, 17.0 mmol) in a similar manner to Example 5, was neutralized by adding 2 mol/L aqueous sodium hydroxide solution (20 ml), and the mixture was filtered to obtain (E)-N-methyl-N-carboxymethyl-4-[2-(1H-indazol-3-yl)vinyl]benzamide (1.04 g, 55%).

Workup

  1. customThe product obtained
  2. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-8afa68c8128846808940bfa9c2fef1a7
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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