Hydrochloric Acid → HCID 53261873, compound

HRID 1404802Notes

Reaction equation

HRID 1404802 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[N:16]=[C:15]3[N:17]([CH2:20][C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)[N:18]=[N:19][C:14]3=[CH:13][CH:12]=2)[CH:8]=[N:7]1)C.[OH-].[Li+].Cl>CO.O>[N:27]1[C:28]2[C:23](=[CH:22][C:21]([CH2:20][N:17]3[C:15]4=[N:16][C:11]([C:9]5[CH:8]=[N:7][N:6]([CH2:5][C:4]([OH:31])=[O:3])[CH:10]=5)=[CH:12][CH:13]=[C:14]4[N:19]=[N:18]3)=[CH:30][CH:29]=2)[CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 53261872HCID 53261872, compound

Product 1

HCID 53261873HCID 53261873, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of Example 154 (0.085 g, 0.218 mmol) in methanol (1.4 ml), lithium hydroxide (0.026 g, 1.09 mmol) in water (0.36 ml) was added and stirred at RT. After 12 h, the pH was adjusted to 7-7.5 using 0.5N HCl and the solid precipitated was filtered, washed with ethyl acetate and petroleum ether and dried under to afford the title compound as a yellow solid (0.034 g, 38%). M.P.: >270° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.87 (d, J=2.7 Hz, 1H), 8.47 (d, J=8.7 Hz, 1H), 8.39 (m, 2H), 8.08 (s, 1H), 8.00 (s. 1H), 7.99 (d, J=7.1 Hz, 1H), 7.82 (t, J=8.9 Hz, 2H), 7.52 (q, J=4.1 Hz, 1H), 6.10 (s, 2H), 4.48 (s, 2H), MS (m/z): 385.87 (M+).

Workup

  1. customthe solid precipitated
  2. filtrationwas filtered
  3. washwashed with ethyl acetate and petroleum ether
  4. customdried under

Sources & evidence

ORD record
ord-d9fc579a2d5f4fa19d32adb00c8b735c
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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