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1-(3-Indolyl)-2-(methylamino)ethanol → HCID 10239708, compound

HRID 23672
Notes
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Reaction equation

HRID 23672 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH:35]([OH:39])[CH2:36][NH:37][CH3:38])=[CH:27]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20][N:37]([CH2:36][CH:35]([OH:39])[C:28]4[C:29]5[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=5)[NH:26][CH:27]=4)[CH3:38])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 343191-(3-Indolyl)-2-(methylamino)ethanolHCID 81531DiisopropylethylamineHCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 10239708HCID 10239708, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.25 mmol), 1-(1H-indol-3-yl)-2-(methylamino)ethanol (Khim.-Farm. Zh. 1970, 4, 5-9)(73 mg, 0.38 mmol) and diisopropylethylamine (67 μL, 0.38 mmol) in dry DMF (5.0 mL) was stirred for 48 hours at 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 at room temp. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile (10 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (112 mg) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-68e08c0fbe734fab99b2bd218a1c1aba
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852731B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes