Toluene → HCID 89784721, compound

HRID 1056010Notes

Reaction equation

HRID 1056010 reaction equation
F[C:2]1[C:3]([CH3:22])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1>>[CH3:22][C:3]1[C:2]([NH:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=2)[N:4]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 104392-AminopyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89784721HCID 89784721, compoundYield 9%

Conditions

Temperature
22 °C

Procedure

Prepared similarly to that described in Example 131 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 61 mg, 0.206 mmol), pyridin-2-amine (97 mg, 1.029 mmol, Aldrich), and KHMDS in toluene (2059 μl, 1.029 mmol) stirring at 22° C. for 1 h. Purification by silica gel (100% DCM to 8% MeOH/DCM) provided 2-(2-methyl-3-(pyridin-2-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (9% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.80 (s, 3H) 2.85 (t, J=6.75 Hz, 2H) 3.44 (dt, J=6.85, 3.42 Hz, 2H) 5.86 (br. s., 1H) 6.99 (br. s., 1H) 7.06 (s, 1H) 7.15 (t, J=5.97 Hz, 1H) 7.53 (t, J=7.82 Hz, 1H) 7.70 (d, J=8.22 Hz, 1H) 7.78-7.83 (m, 1H) 7.86 (dd, J=7.04, 1.76 Hz, 1H) 8.02 (d, J=7.24 Hz, 1H) 8.52 (d, J=3.52 Hz, 1H) 9.32 (s, 1H). MS (ESI, pos. ion) m/z: 371.1 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 8% MeOH/DCM)

Sources & evidence

ORD record
ord-73d685520e4045e2b0701aa2aefd3f95
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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