Hydrochloric Acid → HCID 54670603, compound

HRID 449280Notes

Reaction equation

HRID 449280 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([C:16]2[N:21]=[C:20]3[N:22]([CH2:25][C:26]4[CH:27]=[C:28]5[C:33](=[CH:34][CH:35]=4)[N:32]=[CH:31][CH:30]=[CH:29]5)[N:23]=[N:24][C:19]3=[CH:18][CH:17]=2)[CH:13]=[CH:12][C:3]=1[C:4]([NH:6][CH2:7][C:8]([O:10]C)=[O:9])=[O:5].[OH-].[Li+].Cl>CO.O>[F:1][C:2]1[CH:15]=[C:14]([C:16]2[N:21]=[C:20]3[N:22]([CH2:25][C:26]4[CH:27]=[C:28]5[C:33](=[CH:34][CH:35]=4)[N:32]=[CH:31][CH:30]=[CH:29]5)[N:23]=[N:24][C:19]3=[CH:18][CH:17]=2)[CH:13]=[CH:12][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 54670511HCID 54670511, compound

Product 1

HCID 54670603HCID 54670603, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of Example 50 (0.055 g, 0.113 mmol) in methanol (0.5 ml), lithium hydroxide (0.045 g, 1.05 mmol) in water (0.5 ml) was added and stirred at RT. After 12 h, pH was adjusted to ca. 7 using 0.5N HCl and the solid precipitated was filtered, washed with ethyl acetate and petroleum ether and dried under vacuum to afford the title compound as a pale green solid (0.050 g, 96%). M.P.: 252-254° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 12.70 (s, 1H), 9.01 (d, J=3.9 Hz, 1H), 8.73 (d, J=8.7 Hz, 1H), 8.64 (m, 2H), 8.25 (d, J=8.8 Hz, 1H), 8.20 (m, 4H), 7.97 (d, J=8.9 Hz, 1H), 7.86 (t, J=8.1 Hz, 1H), 7.71 (dd, J=7.8, 4.2 Hz, 1H), 6.27 (s, 2H), 3.96 (d, J=5.8 Hz, 2H). MS (m/z): 456.85 (M+).

Workup

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

Sources & evidence

ORD record
ord-7645ffd39c2945bbbc48b9a5bbc37600
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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