Sodium Hydroxide → HCID 11603236, compound

HRID 2092179Notes

Reaction equation

HRID 2092179 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH2:10][CH2:9][CH:8]2[NH:13][C:14]([NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[N:20][N:21]2C(OC)=O)=[O:15].[OH-].[Na+]>O1CCCC1.CO.O>[NH:21]1[C:22]2[C:18](=[C:17]([NH:16][C:14]([NH:13][CH:8]3[C:7]4[C:12](=[C:3]([C:2]([F:1])([F:31])[F:30])[CH:4]=[CH:5][CH:6]=4)[O:11][CH2:10][CH2:9]3)=[O:15])[CH:25]=[CH:24][CH:23]=2)[CH:19]=[N:20]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 11633454HCID 11633454, compound

Product 1

HCID 11603236HCID 11603236, compoundYield 49.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 37F (0.68 g, 1.56 mmol) in a mixture of 5 ml tetrahydrofuran and 5 ml methanol was treated with sodium hydroxide (5M in methanol, 3 ml, 15 mmol), and the reaction stirred at ambient temperature for 2 hours. The reaction mixture was diluted with water, and the precipitate that formed was collected by filtration. After drying, the solid was purified using reverse-phase HPLC (acetonitrile-water with 0.1% trifluoroacetic acid as eluent) to provide 0.29 g of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 13.01 (s, 1 H), 8.59 (s, 1 H), 8.03 (s, 1 H), 7.67 (d, J=7.46 Hz, 1 H), 7.62 (d, J=7.80 Hz, 1 H), 7.55 (d, J=7.80 Hz, 1 H), 7.22 (t, J=7.80 Hz, 1 H), 7.04-7.11 (m, 2 H), 6.96 (d, J=7.80 Hz, 1 H), 4.96-5.03 (m, 1 H), 4.41-4.49 (m, 1 H), 4.30 (m, 1 H), 2.18 (m, 1 H), 2.06-2.13 (m, 1 H). MS (ESI) m/e 377 (M+H)+. Calcd. For C18H15N4O2F3.0.15 trifluoroacetic acid: C, 55.87; H, 3.88; N, 14.24. Found C, 55.95; H, 3.82; N, 14.28.

Workup

  1. customthe precipitate that formed
  2. filtrationwas collected by filtration
  3. customAfter drying
  4. customthe solid was purified

Sources & evidence

ORD record
ord-256a86a5c1d942579b4e6a6370f6bac9
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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