Sodium Hydroxide → HCID 118235856, compound

HRID 626999Notes

Reaction equation

HRID 626999 reaction equation
[NH2:1][CH:2]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH:38]([F:40])[F:39])[C:3]1[N:7]2[CH:8]=[C:9]([C:12]3[CH:13]=[N:14][C:15]([N:18]4[CH2:23][CH2:22][C:21]([CH3:29])([C:24]([O:26]CC)=[O:25])[CH2:20][CH2:19]4)=[N:16][CH:17]=3)[CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[CH3:30].[OH-].[Na+:42]>C1COCC1.CO>[NH2:1][CH:2]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH:38]([F:39])[F:40])[C:3]1[N:7]2[CH:8]=[C:9]([C:12]3[CH:13]=[N:14][C:15]([N:18]4[CH2:19][CH2:20][C:21]([CH3:29])([C:24]([O-:26])=[O:25])[CH2:22][CH2:23]4)=[N:16][CH:17]=3)[CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[CH3:30].[Na+:42]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118235633HCID 118235633, compound

Product 1

HCID 118235856HCID 118235856, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of Example 300 (0.155 g, 0.2815 mmol) in THF (1 mL) and methanol (1 mL) was added 1.0M aqueous sodium hydroxide solution (0.27 mL, 0.28 mmol) and the mixture was heated at 60° C. for a total of 18 h. The mixture was concentrated in vacuo and re-dissolved in water (10 mL), then frozen and freeze-dried, to afford the title compound (0.138 g, 90%) as an off white solid. δH (400 MHz, DMSO-d6) 8.62 (d, 1H, J 0.2 Hz), 8.54 (s, 2H), 8.04 (m, 1H), 7.42 (m, 3H), 7.11 (m, 1H), 5.87 (m, 1H), 4.32 (m, 2H), 3.25 (m, 2H), 2.42 (d, 2H, J 5.6 Hz), 2.20 (s, 3H), 2.08 (m, 2H), 1.10 (m, 2H), 0.99 (s, 3H). LCMS (pH 3): MH+ 523.8, RT 1.48 minutes.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionre-dissolved in water (10 mL)
  3. temperaturefrozen
  4. customfreeze-dried

Sources & evidence

ORD record
ord-955a84be06c74acfb19388e48f725165
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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