Hydrochloric Acid → HCID 54670603, compound

HRID 1404794Notes

Reaction equation

HRID 1404794 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][NH:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[C:17]3[N:19]([CH2:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)[N:20]=[N:21][C:16]3=[CH:15][CH:14]=2)=[CH:9][C:8]=1[F:33].[OH-].[Li+].Cl>CO.O>[F:33][C:8]1[CH:9]=[C:10]([C:13]2[N:18]=[C:17]3[N:19]([CH2:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)[N:20]=[N:21][C:16]3=[CH:15][CH:14]=2)[CH:11]=[CH:12][C:7]=1[C:6]([NH:5][CH2:4][C:3]([OH:35])=[O:2])=[O:34]

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-c6eb01626cff42a38a8a683f158eb998
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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