Water → HCID 178480017, compound

HRID 629304Notes

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]([C:14]2[C:15]3[CH:24]=[CH:23][N:22](S(C4C=CC(C)=CC=4)(=O)=O)[C:16]=3[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=2)=[CH:12][C:8]2[NH:9][N:10]=[N:11][C:7]=2[CH:6]=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]([C:14]2[C:15]3[CH:24]=[CH:23][NH:22][C:16]=3[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=2)=[CH:12][C:8]2[NH:9][N:10]=[N:11][C:7]=2[CH:6]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 4-[5-(2,4-difluorophenoxy)-1H-1,2,3-benzotriazol-6-yl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (67 mg, 0.12 mmol) in ethanol (7.1 mL) was treated with 3.0 M sodium hydroxide in water (408 μL, 1.22 mmol) and stirred at 20° C. overnight. Purification via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min) gave the desired product (21 mg, 34%). 1H NMR (400 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.01 (br s, 1H), 7.53-7.41 (m, 1H), 7.36 (s, 1H), 7.33-7.21 (m, 2H), 7.16-6.98 (m, 2H), 6.24 (d, J=2.0 Hz, 1H), 3.56 (s, 3H); LCMS calculated for C20H14F2N5O2 (M+H)+: m/z=394.1. found: 394.1.

Workup

customPurification via preparative LCMS (XBridge C18 column
washeluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min)

Sources & evidence

ORD record: ord-95eca40ac88c491da07113212248e665
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315501B2

Reaction notes

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