Methylamine → HCID 59135742, compound

HRID 1960318Notes

Reaction equation

HRID 1960318 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][C:21]([CH2:24][N:25]3[CH2:30][CH2:29][N:28]([CH2:31][C:32]([OH:34])=O)[CH2:27][CH2:26]3)=[CH:22][N:23]=1)=[CH:15]2)(=[O:8])=[O:7].[N:35]1(O)[C:39]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN>CN(C)C=O.C1COCC1.O>[CH3:39][NH:35][C:32](=[O:34])[CH2:31][N:28]1[CH2:29][CH2:30][N:25]([CH2:24][C:21]2[S:20][C:19]([C:16]3[NH:17][C:18]4[C:14]([CH:15]=3)=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][S:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)(=[O:8])=[O:7])=[N:23][CH:22]=2)[CH2:26][CH2:27]1

Participants

8

Reactant 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59135672{4-[(2-{7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetic acid

Product 1

HCID 59135742HCID 59135742, compoundYield 42.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of {4-[(2-{7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetic acid (0.230 g) in N,N-dimethylformamide (4 ml) were added 1H-1,2,3-benzotriazol-1-ol (0.066 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.093 g), and the mixture was stirred at 50° C. for 1 hr. A 2.0 mol/L solution of N-methylamine in THF (0.60 ml) was added to the reaction solution, and the mixture was stirred at 50° C. for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol), and recrystallized from tetrahydrofuran-hexane to give the title compound (0.100 g, yield 42%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at 50° C. for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methanol)
  7. customrecrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-827a7e2e96a048509463d1e5b7ae01f4
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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