Water → HCID 118093980, compound

HRID 1056976Notes

Reaction equation

F[C:2]1C=C(F)C=C[C:3]=1[O:4][C:5]1[N:10]2[N:11]=[C:12]([CH3:14])[CH:13]=[C:9]2[N:8]=[C:7]([CH3:15])[C:6]=1[C:16]1[C:17]2[CH:26]=[CH:25][N:24](S(C3C=CC(C)=CC=3)(=O)=O)[C:18]=2[C:19](=[O:23])[N:20]([CH3:22])[CH:21]=1.[OH-].[Na+].O>C(O)C>[CH2:3]([O:4][C:5]1[N:10]2[N:11]=[C:12]([CH3:14])[CH:13]=[C:9]2[N:8]=[C:7]([CH3:15])[C:6]=1[C:16]1[C:17]2[CH:26]=[CH:25][NH:24][C:18]=2[C:19](=[O:23])[N:20]([CH3:22])[CH:21]=1)[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

A suspension of 4-[7-(2,4-difluorophenoxy)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (29.1 mg, 50.6 μmol) in ethanol (1.0 mL) was treated with a 3.0 M solution of sodium hydroxide in water (0.254 mL, 0.762 mmol), then warmed to 55° C. and stirred at that temperature for 30 min. The reaction mixture was purified via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (6 mg, 14%). 1H NMR (300 MHz, DMSO-d6) δ 12.15 (br s, 1H), 7.28 (d, J=2.8 Hz, 1H), 7.24 (s, 1H), 6.39 (s, 1H), 6.03 (d, J=2.7 Hz, 1H), 4.45 (q, J=7.0 Hz, 2H), 3.55 (s, 3H), 2.42 (s, 3H), 2.24 (s, 3H), 1.07 (t, J=7.1 Hz, 3H); LCMS calculated for C18H20N5O2 (M+H)+: m/z=338.2. found: 338.1.

Workup

customThe reaction mixture was purified via preparative LCMS (XBridge C18 column
washeluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record: ord-5a105f1a901a48b9bc3e56957cb03237
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399640B2

Reaction notes

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