Dimethylformamide → HCID 59258980, compound

HRID 641693Notes

Reaction equation

HRID 641693 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:19](=[O:20])[N:18]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:9]2[N:10]=[C:11](S(C)=O)[N:12]=[C:13]([CH3:14])[C:8]=2[CH:7]=1)=[O:5])[CH3:2].CN.C[CH2:29][N:30](CC)CC.CN(C=O)C>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:19](=[O:20])[N:18]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:9]2[N:10]=[C:11]([NH:30][CH3:29])[N:12]=[C:13]([CH3:14])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 8471TriethylamineHCID 59258972HCID 59258972, compound

Product 1

HCID 59258980HCID 59258980, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of example 87 (16.0 g, 0.044 mol), methylamine (10.15 g, 0.088 mol, 27% in EtOH), Et3N (8.9 g, 0.088 mol) and a catalytic amount of DMF in acetonitrile (60 mL) was refluxed for 48 hours under a N2 balloon. TLC (petroleum ether/EtOAc 1:2) indicated the starting material was consumed completely. The reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc from 15:1 to 4:1) to yield the crude product. Re-crystallization from CH2Cl2/petroleum ether (10 mL/150 mL) afforded pure title compound (10.5 g, 72.2%) as a white solid.

Workup

  1. customwas consumed completely
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe residue was purified by column chromatography (silica gel, petroleum ether/EtOAc from 15:1 to 4:1)
  4. customto yield the crude product

Sources & evidence

ORD record
ord-8be904f18dc945a999982f88c430bbe6
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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