Diisopropylethylamine → HCID 71730508, compound

HRID 1056221Notes

Reaction equation

HRID 1056221 reaction equation
[C:1]([NH:5][C:6]1[C:7](F)=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=[O:25])[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].Cl.CN.C[CH2:31][N:32](C(C)C)C(C)C>CS(C)=O.C(Cl)Cl>[C:1]([NH:5][C:6]1[C:7]([NH:32][CH3:31])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=[O:25])[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 71730507HCID 71730507, compound

Product 1

HCID 71730508HCID 71730508, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-(tert-butylamino)-2-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (343) (16 mg, 0.04 mmol), methanamine hydrochloride (15 mg, 0.22 mmol, Sigma-Aldrich), and DIEA (47.4 μL, 0.27 mmol) in DMSO (0.45 mL) was stirred at RT for 2 h. The reaction mixture was diluted with DCM (100 mL), added to a separatory funnel, and washed with saturated aq. NaHCO3 (2×75 mL) before the organic layer was separated, dried over Na2SO4, and concentrated. The crude product was adsorbed onto silica and was purified via automated flash chromatography (silica gel) with 1-4% of 2 M NH3 in MeOH/DCM to give 2-(3-(tert-butylamino)-2-(methylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4 (5H)-one (344) (4 mg, 24% yield) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (s, 9H) 2.85 (t, J=6.85 Hz, 2H) 2.95 (d, J=4.30 Hz, 3H) 3.42 (td, J=6.80, 2.45 Hz, 2H) 6.32 (s, 1H) 6.89 (d, J=2.15 Hz, 1H) 6.90 (br. s., 1H) 7.17 (t, J=7.63 Hz, 1H) 7.28 (dd, J=8.02, 1.37 Hz, 1H) 7.30-7.33 (m, 1H) 7.51 (dd, J=7.63, 1.37 Hz, 1H) 12.10 (br. s., 1H). MS (ESI, pos. ion) m/z: 365.3 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with saturated aq. NaHCO3 (2×75 mL) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customwas purified

Sources & evidence

ORD record
ord-a442e41b3d1844f29883a23bc332ad2a
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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