Diisopropylethylamine → HCID 71730510, compound

HRID 1056224Notes

Reaction equation

HRID 1056224 reaction equation
[C:1]([NH:5][C:6]1[C:7](Cl)=[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.[NH:28]1[CH2:31][CH:30]([OH:32])[CH2:29]1.C(N(C(C)C)C(C)C)C>CS(C)=O.C(Cl)Cl>[C:1]([NH:5][C:6]1[C:7]([N:28]2[CH2:31][CH:30]([OH:32])[CH2:29]2)=[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 27592903-Hydroxyazetidine hydrochlorideHCID 71730509HCID 71730509, compound

Product 1

HCID 71730510HCID 71730510, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-(tert-butylamino)-2-chloroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (345) (28 mg, 0.07 mmol), azetidin-3-ol hydrochloride (41 mg, 0.37 mmol, Matrix Scientific, Columbia, S.C.), and N-ethyl-N-isopropylpropan-2-amine (81 pt, 0.45 mmol) in DMSO (0.75 mL) was stirred at 50° C. for 1 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 1-5% of 2 M NH3 in MeOH/DCM to give 2-(3-(tert-butylamino)-2-(3-hydroxyazetidin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (346) (19 mg, 61% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (s, 9H) 2.85 (t, J=6.94 Hz, 2H) 3.43 (td, J=6.75, 2.35 Hz, 2H) 3.94 (dd, J=9.00, 5.09 Hz, 2H) 4.41 (dd, J=8.80, 6.85 Hz, 2H) 4.57 (sxt, J=5.91 Hz, 1H) 5.64-5.71 (m, 2H) 6.95 (s, 1H) 6.96 (s, 1H) 7.24 (t, J=7.82 Hz, 1H) 7.36 (dd, J=7.92, 1.27 Hz, 1H) 7.61 (dd, J=7.43, 1.37 Hz, 1H) 12.00 (s, 1H). MS (ESI, pos. ion) m/z: 407.1 (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-3336df44d21e4f289894975af021af4b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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