Water → HCID 178485535, compound

Participants

Reaction Conditions

Reaction Steps

2-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-5-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluoro-N-methylbenzamide (225 mg, 0.321 mmol) was dissolved in dioxane (6 mL), 6N NaOH (2 mL) and water (2 mL) was added in a microwave safe vessel. The reaction was then heated in a microwave at 120° C. for 23 min. Reaction was diluted with EtOAc and the organic layer was washed with water and a saturated brine solution and dried over sodium sulfate. Solvents were removed under reduced pressure and the residue purified by chromatography on SiO2 to afford 2-[(2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-5-methyl-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide (124 mg, 0.227 mmol) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 6 H) 2.41 (s, 3 H) 2.81 (d, J=4.39 Hz, 3 H) 3.12 (t, J=8.24 Hz, 2 H) 3.17 (s, 2 H) 3.76 (s, 3 H) 4.18 (t, J=8.33 Hz, 2 H) 6.68 (s, 1 H) 6.86 (t, J=9.25 Hz, 1 H) 6.95 (s, 1 H) 7.25 (d, J=7.14 Hz, 1 H) 7.52 (s, 1 H) 8.45 (d, J=8.42 Hz, 1 H) 8.57 (s, 1 H) 8.66 (d, J=4.39 Hz, 1 H) 9.44 (s, 1 H) 10.92 (s, 1 H). ESIMS (M+H)+=547.

Provenance & Evidence