Diisopropylethylamine → HCID 178461976, compound

HRID 75323

Reaction equation

HRID 75323 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[N:7][C:8]([C@@H:18]([NH2:20])[CH3:19])=[C:9]([C:12]3[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=3)[CH:10]=2)[CH:5]=[CH:4]1.Cl[C:22]1[N:30]=[C:29]([NH2:31])[N:28]=[C:27]2[C:23]=1[N:24]=[CH:25][NH:26]2.C(N(C(C)C)C(C)C)C>C(#N)C>[CH3:2][N:3]1[C:11]2[C:6](=[N:7][C:8]([C@@H:18]([NH:20][C:22]3[N:30]=[C:29]([NH2:31])[N:28]=[C:27]4[C:23]=3[N:24]=[CH:25][NH:26]4)[CH3:19])=[C:9]([C:12]3[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=3)[CH:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86708027(S)-1-(1-Methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine hydrochlorideHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 178461976HCID 178461976, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

(S)-1-(1-Methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine hydrochloride (500 mg, 1.71 mmol), 6-chloro-9H-purin-2-amine (436 mg, 2.57 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.895 mL, 5.14 mmol) were combined in acetonitrile (10 mL). The reaction mixture was heated in a microwave reactor at 120° C. for 2 hours and then concentrated. The residue was diluted with MeOH/DMSO and purified by preparative HPLC (basic mode) eluting with 20-30% ACN in water. The fractions containing the desired compound were collected and concentrated in vacuo. The residue was re-crystallized in an EtOAc/MeOH/hexane mixture to give the title compound (295 mg, 44.4%). 1H NMR (500 MHz, CD3OD) δ ppm 1.50 (d, J=6.83 Hz, 3 H), 3.59-3.66 (m, 3 H), 3.89 (br s, 3 H), 5.56 (br s, 1 H), 6.45 (d, J=1.95 Hz, 1 H), 6.68-6.73 (m, 1 H), 7.58-7.65 (m, 2 H), 7.77-7.89 (m, 2 H); ESI-MS m/z [M+H]+ calc'd for C19H20N10, 389; found 389.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with MeOH/DMSO
  3. custompurified by preparative HPLC (basic mode)
  4. washeluting with 20-30% ACN in water
  5. additionThe fractions containing the desired compound
  6. customwere collected
  7. concentrationconcentrated in vacuo
  8. customThe residue was re-crystallized in an EtOAc/MeOH/hexane mixture

Sources & evidence

ORD record
ord-af0c6095bc1f40a4a4a89f48baab4d91
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Linked notes

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