Sodium Hydroxide → HCID 11626031, compound

HRID 2092181Notes

Reaction equation

HRID 2092181 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH:10]2[CH2:19][NH:20][C:21]([NH:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[N:27][N:28]3C(OC)=O)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O>[NH:28]1[C:29]2[C:25](=[C:24]([NH:23][C:21]([NH:20][CH2:19][CH:10]3[CH2:11][CH2:12][C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:9]3[CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:22])[CH:32]=[CH:31][CH:30]=2)[CH:26]=[N:27]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11518665HCID 11518665, compound

Product 1

HCID 11626031HCID 11626031, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product from Example 53A (0.1913 g, 0.40 mmol) was dissolved in methanol (5 mL). A NaOH solution (1.0 mL, 5 M in methanol) was added and stirred for 30 minutes. The reaction mixture was then diluted with water until a precipitate formed. The solid was collected by filtration, washed with water and dried under vacuum to afford the title compound (0.1294 g, 76%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.98 (s, 1 H) 8.69 (s, 1 H) 8.07 (s, 1 H) 7.60 (d, J=7.46 Hz, 1 H) 7.24 (m, 6 H) 7.04 (m, 2 H) 6.94 (d, J=6.44 Hz, 1 H) 6.71 (d, J=8.14 Hz, 1 H) 6.51 (t, J=6.95 Hz, 2 H) 3.71 (m, 1 H) 3.37 (m, 3 H) 3.11 (m, 1 H) 2.83 (m, 3 H) 2.62 (m, 1 H) 1.87 (m, 1 H) 1.54 (m, 1 H). MS (ESI) m/z 426 (M+H)+, 424 (M−H)−. Calcd For C26H27N5O: C, 73.39; H, 6.40; N, 16.46. Found C, 73.22; H, 6.36; N, 16.30.

Workup

  1. customformed
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-dba2effdad7b49419007d383d669183b
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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