Water → HCID 118093964, compound

HRID 1056939Notes

Reaction equation

HRID 1056939 reaction equation
[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:3]=1[O:4][C:5]1[C:13]2[NH:12][C:11](=[O:14])[N:10]([CH3:15])[C:9]=2[CH:8]=[CH:7][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>[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:3]=1[O:4][C:5]1[C:13]2[NH:12][C:11](=[O:14])[N:10]([CH3:15])[C:9]=2[CH:8]=[CH:7][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

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 118093812HCID 118093812, compound

Product 1

HCID 118093964HCID 118093964, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(2,4-difluorophenoxy)-1-methyl-5-{6-methyl-1-[(4-methylphenyl)sulfonyl]-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one (20.0 mg, 0.0347 mmol) in ethanol (2.0 mL) was treated with 3.0 M Sodium hydroxide in water (116 μL, 0.347 mmol) and stirred at RT overnight. The reaction mixture was purified 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) to give the desired product (14.5 mg, 99%). 1H NMR (400 MHz, DMSO-d6) δ 11.94 (s, 1H), 11.25 (s, 1H), 7.25-7.06 (m, 5H), 6.74-6.62 (m, 1H), 6.51-6.38 (m, 1H), 6.14-6.05 (m, 1H), 3.44 (s, 3H), 3.34 (s, 3H); LCMS calculated for C22H17F2N4O3 (M+H)+: m/z=423.1. found: 423.1.

Workup

  1. customThe reaction mixture was purified via preparative LCMS (XBridge C18 column
  2. washeluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-ec3de186c1814fe181166fc368960155
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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