Hydrochloric Acid → HCID 66994486, compound

HRID 1404782Notes

Reaction equation

HRID 1404782 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C:20]4[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=4[Cl:28])[N:17]=[N:18][C:13]3=[CH:12][CH:11]=2)=[CH:6][C:5]=1[F:29].[OH-].[Na+].Cl>CO.C1COCC1.O>[Cl:28][C:21]1[C:22]([F:27])=[CH:23][CH:24]=[C:25]([F:26])[C:20]=1[CH2:19][N:16]1[C:14]2=[N:15][C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[C:5]([F:29])[CH:6]=3)=[CH:11][CH:12]=[C:13]2[N:18]=[N:17]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66994916HCID 66994916, compound

Product 1

HCID 66994486HCID 66994486, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 17 (0.300 g, 0.725 mmol) in methanol (1 ml), THF (2 ml), sodium hydroxide (0.150 g, 3.75 mmol) in water (1 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 vacuum to afford the title compound as a pale brown solid (0.120 g, 41%). M.P.: 211-213° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.65 (d, J=8.8 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 8.02 (m, 2H), 7.83 (t. J=7.4 Hz, 1H). 7.60 (dt, J=9.1, 4.8 Hz, 1H), 7.46 (dt, J=9.0, 4.0 Hz, 1H), 6.11 (s, 2H), MS (m/z): 418.70 (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-4df3b7c2aa2248db8b9aa053043b54d2
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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