m-Toluidine → HCID 89783913, compound

HRID 1055874Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>>[CH3:22][C:23]1[CH:24]=[C:25]([NH:26][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([C:12]4[NH:20][C:19]5[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=5[CH:13]=4)[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:27]=[CH:28][CH:29]=1

Participants

Reactant 4

HCID 7934m-Toluidine

HCID 8028Tetrahydrofuran

HCID 2733832Lithium Hexamethyldisilazide

HCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783913HCID 89783913, compoundYield 4%

Procedure

Prepared according to Example 102, using 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50 mg, 0.168 mmol), 3-methylaniline (91 μl, 0.840 mmol, Sigma Aldrich), and 1.0 M LHMDS in THF (163 μl, 0.840 mmol, Sigma Aldrich) and stirring at 25° C. for 2.h. Purification by column chromatography (silica gel: 0 to 4% MeOH/DCM) provided 2-(2-((3-methylphenyl)amino)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (2.5 mg, 4%). 1H NMR (400 MHz, MeOH-d4) δ ppm 7.84-7.90 (2H, m) 7.37-7.43 (1H, m) 7.27-7.32 (2H, m) 7.17 (3H, s) 6.88 (2H, m) 3.40 (2H, t, J=1.00 Hz) 2.50 (2H, t, J=1.00 Hz) 2.24 (3H, s). m/z (ESI, +ve) 369.2 (M+H)+.

Workup

customPrepared
customPurification by column chromatography (silica gel: 0 to 4% MeOH/DCM)

Sources & evidence

ORD record: ord-b6f35df09a5d4b8ca1e8870a50c1b7c7
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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