2-(Dimethylamino)ethanol → HCID 22467222, compound

HRID 1934598Notes

Reaction equation

HRID 1934598 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[CH2:4][CH2:5]CN=C=NCC.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]([C:38]3[C:46]4[C:41](=[CH:42][C:43]([C:47]([OH:49])=[O:48])=[CH:44][CH:45]=4)[N:40]([CH3:50])[CH:39]=3)[C:23]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=3[O:36][CH3:37])(=[O:28])=[O:27])=[O:24])=[CH:21][C:16]=2[O:15][CH2:14]1.CN(CCO)C>C(Cl)Cl.CN(C=O)C>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]([C:38]3[C:46]4[C:41](=[CH:42][C:43]([C:47]([O:49][CH2:5][CH2:4][N:3]([CH3:12])[CH3:2])=[O:48])=[CH:44][CH:45]=4)[N:40]([CH3:50])[CH:39]=3)[C:23]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=3[O:36][CH3:37])(=[O:27])=[O:28])=[O:24])=[CH:21][C:16]=2[O:15][CH2:14]1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22009947HCID 22009947, compound

Product 1

HCID 22467222HCID 22467222, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (128 mg, 0.67 mmol) was added to a stirred solution of 3-{1-(1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-6-indolecarboxylic acid (the product of Example 17, 300 mg, 0.56 mmol), N,N-dimethylaminopyridine (75 mg, 0.61 mmol) and dimethylaminoethanol (0.17 ml, 1.67 mmol) in a mixture of CH2Cl2 (9 ml) and DMF (0.5 ml) at room temperature under a nitrogen atmosphere. After 12 h a fine white precipitate had formed. The product was removed by filtration and washed with cold methanol.

Workup

  1. customAfter 12 h a fine white precipitate had formed
  2. customThe product was removed by filtration
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-e96dc055d0c34921a2710a1f3fa2e79c
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

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