Diisopropylethylamine → HCID 44432280, compound

HRID 23626

Reaction equation

HRID 23626 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.[CH3:26][NH:27][CH2:28][C@H:29]([C:31]1[N:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[OH:30].C(N(C(C)C)CC)(C)C>COCCOC>[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][N:27]([CH2:28][C@@H:29]([OH:30])[C:31]4[N:32]=[CH:33][CH:34]=[CH:35][N:36]=4)[CH3:26])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideHCID 69731156HCID 69731156, compound

Product 1

HCID 44432280HCID 44432280, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (195 mg, 0.49 mmol), (1R)-2-(methylamino)-1-pyrimidin-2-ylethanol (Preparation 104, 168 mg, 0.74 mmol) and diisopropylethylamine (430 μL, 2.5 mmol) in dry DME (10 mL) was heated to 60° C., becoming a solution. The reaction was stirred overnight at that temperature. After cooling to room temperature, the solution was diluted with ice water (30 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 (30 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (105 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 at room temp
  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 (30 mL
  10. dissolutiondissolved
  11. temperaturewith warming
  12. temperaturecooled to 0° C. overnight)

Sources & evidence

ORD record
ord-ebb88e45327046bc86aa9a78392502c2
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

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