Trifluoroacetic acid → N-(1-hydroxy-2-methylpropan-2-yl)-2-(1-methyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

To a solution of N-(1-hydroxy-2-methylpropan-2-yl)-2-(1-methyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (26 mg, 56.6 mol) in dichloromethane (1 mL) was added trifluoroacetic acid (129 mg, 87.2 μL, 1.13 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (1 mL), methanol (0.5 mL) and ammonium hydroxide (0.15 mL) and stirred at room temperature for 2 h. The mixture was concentrated and triturated with water. The solid was collected by filtration and washed with water and ether to give N-(1-hydroxy-2-methylpropan-2-yl)-2-(1-methyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (12 mg, 36.4 mol, 64%) as a brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.19 (s, 1H), 9.16 (s, 1H), 8.01 (s, 1H), 7.91 (d, J=3.0, 1 H), 7.86 (s, 1H), 7.70 (s, 1H), 7.49 (s, 1H), 5.15 (t, J=5.7, 1 H), 3.82 (s, 3H), 3.57 (d, J=5.9, 2 H), 1.37 (s, 9H); MS (EI/CI) m/z: 330.2 [M+H].

1. concentrationThe reaction mixture was concentrated in vacuo
2. customthe residue obtained
3. stirringstirred at room temperature for 2 h
4. concentrationThe mixture was concentrated
5. customtriturated with water
6. filtrationThe solid was collected by filtration
7. washwashed with water and ether

ORD record

ord-aef89f2f94094a039210fd685905dcd4

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334278B2