Diisopropylethylamine → HCID 178503445, compound

HRID 75299Notes

Reaction equation

HRID 75299 reaction equation
Cl.Cl.[CH3:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C@@H:19]([NH2:21])[CH3:20])=[C:10]([C:13]3[C:14]([CH3:18])=[N:15][NH:16][CH:17]=3)[CH:11]=2)[CH:6]=[CH:5]1.Cl[C:23]1[C:28]([C:29]#[N:30])=[C:27]([CH3:31])[N:26]=[C:25]([S:32][CH3:33])[N:24]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[CH3:31][C:27]1[C:28]([C:29]#[N:30])=[C:23]([NH:21][C@H:19]([C:9]2[N:8]=[C:7]3[CH:6]=[CH:5][N:4]([CH3:3])[C:12]3=[CH:11][C:10]=2[C:13]2[C:14]([CH3:18])=[N:15][NH:16][CH:17]=2)[CH3:20])[N:24]=[C:25]([S:32][CH3:33])[N:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 582963084-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrileHCID 178434491HCID 178434491, compound

Product 1

HCID 178503445HCID 178503445, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (S)-1-(1-methyl-6-(3-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine dihydrochloride (200 mg, 0.609 mmol), 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile (182 mg, 0.914 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.318 mL, 1.83 mmol) in acetonitrile (5 mL) was heated in a microwave reactor at 120° C. for 2 hours. The mixture was then concentrated. The residue was dissolved in MeOH/DCM, absorbed onto silica gel, and purified by column chromatography eluting with 20-80% EtOAc in hexane over 60 minutes to give the title compound. ESI-MS m/z [M+H]+ calc'd for C21H22N8S, 419; found 419.

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutionThe residue was dissolved in MeOH/DCM
  3. customabsorbed onto silica gel
  4. custompurified by column chromatography
  5. washeluting with 20-80% EtOAc in hexane over 60 minutes

Sources & evidence

ORD record
ord-3c8b57ea98594fff82561bfe6cc61e84
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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