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1-(3-Indolyl)-2-(methylamino)ethanol → HCID 10311734, compound

HRID 982724
Notes
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Reaction equation

HRID 982724 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[S:19][C:18]([CH2:20]Cl)=[CH:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH:34]([OH:38])[CH2:35][NH:36][CH3:37])=[CH:26]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[S:19][C:18]([CH2:20][N:36]([CH2:35][CH:34]([OH:38])[C:27]4[C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[NH:25][CH:26]=4)[CH3:37])=[CH:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 343191-(3-Indolyl)-2-(methylamino)ethanolHCID 81531DiisopropylethylamineHCID 22563229N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 10311734HCID 10311734, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.26 mmol), 1-(1H-indol-3-yl)-2-(methylamino)ethanol (Khim.-Farm. Zh. 1970, 4, 5-9)(75 mg, 0.39 mmol) and diisopropylethylamine (180 μL, 1.04 mmol) in dry DMF (5 mL) was heated to 60° C., becoming a solution. The reaction was stirred for 5 hours at that temperature. After cooling to room temperature, the solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight in the refrigerator. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile/water (dissolved with warming 5 mL of acetonitrile, then cooled to 0° C. and then diluted with 3 mL of water, left overnight) gave the title compound (59 mg) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringThe resulting milky suspension was stirred vigorously for 30 minutes
  3. waitleft
  4. waitstanding overnight in the refrigerator
  5. filtrationThe mixture was filtered
  6. washthe collected solid was washed with water
  7. customdried in vacuo
  8. customleaving a white solid
  9. customRecrystallization from acetonitrile/water (
  10. dissolutiondissolved
  11. temperaturewith warming 5 mL of acetonitrile
  12. temperaturecooled to 0° C.
  13. additiondiluted with 3 mL of water
  14. waitleft overnight)

Sources & evidence

ORD record
ord-b88de20f45ee400eb7d50f0d510cb8f5
Source dataset
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06861438B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes