3-Aminopyridine → HCID 89784574, compound

HRID 1055868Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.ClC1C=C[C:16]2[C:11](=[CH:12][C:13]([C:19]3[NH:27][C:26]4[CH2:25][CH2:24][NH:23][C:22](=[O:28])[C:21]=4[CH:20]=3)=[CH:14][CH:15]=2)N=1.[Li+].C[Si]([N-:34][Si](C)(C)C)(C)C.[CH2:39]1[CH2:43]OC[CH2:40]1>>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:43]2[CH:39]=[CH:40][C:11]3[C:12](=[C:13]([C:19]4[NH:27][C:26]5[CH2:25][CH2:24][NH:23][C:22](=[O:28])[C:21]=5[CH:20]=4)[CH:14]=[CH:15][CH:16]=3)[N:34]=2)[CH:3]=1

Participants

Reactant 3

HCID 100093-Aminopyridine

HCID 23714775LiHMDS tetrahydrofuran

HCID 89784225HCID 89784225, compound

Product 1

HCID 89784574HCID 89784574, compoundYield 34.3%

Conditions

Temperature: 25 °C

Procedure

Prepared according to Example 102, using 3-aminopyridine (166 mg, 1.763 mmol, Sigma Aldrich), 2-(2-chloroquinolin-7-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 105 mg, 0.353 mmol), and 1.0 M LHMDS THF (1763 μl, 1.763 mmol, Sigma Aldrich) and stirring for 2.5 h at 25° C. Purification by washing of the mixture with saturated aq. NH4Cl provided 2-(2-(3-pyridinylamino)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (43 mg, 34%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.86-11.91 (1H, m) 9.69-9.72 (1H, m) 8.81-8.85 (1H, m) 8.24-8.32 (2H, m) 8.13-8.19 (1H, m) 7.86-7.91 (1H, m) 7.60-7.66 (1H, m) 7.36-7.41 (1H, m) 7.29-7.36 (1H, m) 7.08-7.15 (1H, m) 6.89-6.95 (1H, m) 6.81-6.86 (1H, m) 3.38-3.46 (2H, m) 2.73 (2H, s). m/z (ESI, +ve) 356.1 (M+H)+.

Workup

customPrepared
customPurification
washby washing of the mixture with saturated aq. NH4Cl

Sources & evidence

ORD record: ord-c123fd3f156c47fe8e039f91e2ba86ec
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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