Methanol → HCID 71730637, compound

HRID 1056229Notes

Reaction equation

HRID 1056229 reaction equation
F[B-](F)(F)F.[CH3:6][O+:7]([CH3:9])C.[C:10]([NH:14][C:15]1[C:16]([CH3:35])=[N:17][C:18]2[C:23]([N:24]=1)=[C:22]([C:25]1[NH:33][C:32]3[CH2:31][CH2:30][NH:29]C(=O)[C:27]=3[CH:26]=1)[CH:21]=[CH:20][CH:19]=2)([CH3:13])([CH3:12])[CH3:11].CO>C(Cl)Cl>[C:10]([NH:14][C:15]1[C:16]([CH3:35])=[N:17][C:18]2[C:23](=[C:22]([C:25]3[NH:33][C:32]4[CH2:31][CH2:30][N:29]=[C:6]([O:7][CH3:9])[C:27]=4[CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[N:24]=1)([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 71731146HCID 71731146, compound

Product 1

HCID 71730637HCID 71730637, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethyloxonium tetrafluoroborate (239 mg, 1.617 mmol, Sigma-Aldrich) was added to a red slurry of 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (193, 113 mg, 0.32 mmol) in DCM (10 mL) and the resulting mixture was stirred at RT for 1 h when the solid had begun to stick to the side of the flask; MeOH (2 mL) was added to bring all the solid into solution and stir at RT for 16 h when a mixture of product and starting material was observed via lcms. The crude product was adsorbed onto silica and was purified via automated flash chromatography (silica gel) with 100% DCM to 4% 2 M NH3 in MeOH/DCM to give N-(tert-butyl)-8-(4-methoxy-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-3-methylquinoxalin-2-amine (351, 16 mg, 14% yield) as a rust colored solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.66 (s, 9H) 2.55 (s, 3H) 2.82 (t, J=7.73 Hz, 2H) 3.84 (t, J=7.73 Hz, 2H) 3.88 (s, 3H) 4.84 (s, 1H) 6.80 (d, J=1.96 Hz, 1H) 7.36 (t, J=7.82 Hz, 1H) 7.63 (dd, J=8.12, 1.27 Hz, 1H) 7.91 (dd, J=7.63, 1.37 Hz, 1H) 12.54 (br. s., 1H). 13C NMR (101 MHz, CDCl3) δ ppm 21.30, 21.51, 28.68, 46.23, 51.32, 52.37, 100.94, 110.83, 124.51, 124.72, 125.43, 126.11, 131.26, 135.55, 136.41, 136.91, 145.19, 148.40, 161.58. MS (ESI, pos. ion) m/z: 364.4 (M+1).

Workup

  1. stirringstir at RT for 16 h when
  2. additiona mixture of product
  3. customwas purified

Sources & evidence

ORD record
ord-94710d96ea9d47d8b7d38b11677ada6d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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