Water → 4-[4-(2,4-Difluorophenoxy)-1H-1,2,3-benzotriazol-5-yl]-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 1056942Notes

Reaction equation

[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[O:4][C:5]1[C:13]2[N:12]=[N:11][NH:10][C:9]=2[CH:8]=[CH:7][C:6]=1[C:14]1[C:15]2[CH:24]=[CH:23][N:22](S(C3C=CC(C)=CC=3)(=O)=O)[C:16]=2[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=1.[OH-].[Na+].O>C(O)C>[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[O:4][C:5]1[C:13]2[N:12]=[N:11][NH:10][C:9]=2[CH:8]=[CH:7][C:6]=1[C:14]1[C:15]2[CH:24]=[CH:23][NH:22][C:16]=2[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 4-[4-(2,4-difluorophenoxy)-1H-1,2,3-benzotriazol-5-yl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (32 mg, 0.058 mmol) in ethanol (3.4 mL) was treated with 3.0 M sodium hydroxide in water (195 μL, 0.584 mmol) and stirred at 20° C. for 15 h. 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 (13 mg, 56%). 1H NMR (400 MHz, DMSO-d6) δ 12.05 (s, 1H), 7.77 (br s, 1H), 7.53 (d, J=8.5 Hz, 1H), 7.37-7.19 (m, 3H), 6.77 (br s, 2H), 6.23-6.07 (m, 1H), 3.50 (s, 3H); LCMS calculated for C20H14F2N5O2 (M+H)+: m/z=394.1. found: 394.0.

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-5fe3d45a737241debe88a7ee66d9ccdc
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399640B2

Reaction notes

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