Diisopropylethylamine → HCID 59985229, compound

HRID 23633

Reaction equation

HRID 23633 reaction equation
[F: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[CH:36]=[N:35][CH:34]=[CH:33][N:32]=1)[OH:30].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[F: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[CH:36]=[N:35][CH:34]=[CH:33][N:32]=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

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 10285809(1R)-2-(methylamino)-1-pyrazin-2-ylethanolHCID 22574387N-(4-fluorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 59985229HCID 59985229, compoundYield 22.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-fluorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (104 mg, 0.275 mmol), (1R)-2-(methylamino)-1-pyrazin-2-ylethanol (Preparation 80, 65 mg, 0.0.42 mmol) and diisopropylethylamine (72 μL, 0.0.41 mmol) in dry DMF (5.5 mL) was stirred at room temperature for 17 hours. The solution was then diluted with water (20 mL). The resulting precipitate was collected by filtration and the collected solid was dried in vacuo, providing a white solid. Attempted recrystallization from acetonitrile (20 mL, dissolved with warming and then cooled to room temperature) gave the title compound (31 mg) as a white solid upon concentrating the filtrate.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customthe collected solid was dried in vacuo
  3. customproviding a white solid
  4. customAttempted recrystallization from acetonitrile (20 mL
  5. dissolutiondissolved
  6. temperaturewith warming
  7. temperaturecooled to room temperature)

Sources & evidence

ORD record
ord-aee10b747c794fb3bccbcc707476cc3b
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

Loading…