Sodium Hydroxide → HCID 18975436, compound

HRID 2393410Notes

Reaction equation

HRID 2393410 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:33])[NH:11][C:12]2[CH:28]=[CH:27][C:26]3[C:17]4[NH:18][C:19](=[O:25])[C:20]5[N:21]([CH:22]=[CH:23][N:24]=5)[C:16]=4[C:15](=[CH:29][C:30]([OH:32])=[O:31])[C:14]=3[CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>O>[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:33])[NH:11][C:12]2[CH:28]=[CH:27][C:26]3[C:17]4[NH:18][C:19](=[O:25])[C:20]5[N:21]([CH:22]=[CH:23][N:24]=5)[C:16]=4[CH:15]([CH2:29][C:30]([OH:32])=[O:31])[C:14]=3[CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86753088HCID 86753088, compound

Product 1

HCID 18975436HCID 18975436, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The process is performed as in Example 62 but starting with 0.3 g of 8-[3-(3-fluorophenyl)ureido]-10-(carboxymethylene)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one hydrochloride, 15 ml of water and 1 ml of 1N sodium hydroxide. After removal of the catalyst, the filtrate is acidified with 2 ml of 1N hydrochloric acid and the precipitate formed is filtered off, washed with distilled water and dried under vacuum (1 mnHg; 0.13 kPa). 0.14 g of 8-[3-(3-fluorophenyl)ureido]-10-(carboxymethyl)-5H,10H-imidazo[1,2-a)indeno[1,2-e]pyrazin-4-one hydrochloride is obtained in the form of a light brown solid melting above 260° C. (1H NMR spectrum (300 MHz; (CD3)2SO-d6 ; δ in ppm]: 2.60 and 3.27 (2 dd, J=16.5 and 9 Hz and J=16.5 and 3.5 Hz respectively, 1H each: CH2); 4.47 (dd, J=9 Hz and 3.5 Hz, 1H: CH 10); 6.80 (dt, J=8.5 and 2 Hz, 1H: aromatic H ortho to the F and para to the ureido); 7.13 (broad d, J=8.5 Hz, 1H: aromatic H para to the F and ortho to the ureido); 7.32 (dt, J=8.5 and 8 Hz, 1H: aromatic H meta to the F and meta to the ureido); 7.44 (dd, J=8.5 and 1.5 Hz, 1H: H 7); 7.53 (d mt, J=12 Hz, 1H: aromatic H ortho to the F and ortho to the ureido); 7.75 and 8.26 (2 broad s, 1H each: H of the imidazole); 7.79 (d, J=8.5 Hz, 1H: H 6), 7.87 (broad s, 1H: H 9); 9.18 and 9.23 (2 broad s, 1H each: NHCONH); 12.65 (s 1H: NH 5)).

Workup

  1. customAfter removal of the catalyst
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with distilled water
  5. customdried under vacuum (1 mnHg; 0.13 kPa)

Sources & evidence

ORD record
ord-a8d511aa3c804200916cab72017ac045
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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