Fumaric Acid → HCID 131715086, compound

HRID 1906676Notes

Reaction equation

HRID 1906676 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=2)=[CH:16][CH:15]=1)=[O:12])C1C=CC=CC=1.[CH:28]1([CH2:31][O:32][CH2:33][CH2:34][C:35]2[CH:45]=[CH:44][C:38]([O:39][CH2:40][CH:41]3[O:43][CH2:42]3)=[CH:37][CH:36]=2)[CH2:30][CH2:29]1.[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]/[C:49]([OH:51])=[O:50]>C(O)CC>[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]/[C:49]([OH:51])=[O:50].[OH:43][CH:41]([CH:40]([CH2:46][C:47]1[CH:11]=[CH:10][CH:9]=[CH:49][CH:48]=1)[O:39][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][CH2:33][O:32][CH2:31][CH:28]2[CH2:29][CH2:30]2)=[CH:45][CH:44]=1)[CH2:1][NH:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=2)=[CH:18][CH:19]=1)=[O:12].[OH:43][CH:41]([CH:40]([CH2:46][C:47]1[CH:19]=[CH:14][CH:15]=[CH:49][CH:48]=1)[O:39][C:38]1[CH:44]=[CH:45][C:35]([CH2:34][CH2:33][O:32][CH2:31][CH:28]2[CH2:30][CH2:29]2)=[CH:36][CH:37]=1)[CH2:42][NH:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=2)=[CH:18][CH:19]=1)=[O:12]

Participants

5

Reactant 3

HCID 444972Fumaric AcidHCID 117915422-((4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)methyl)oxiraneHCID 14003355HCID 14003355, compound

Product 1

HCID 131715086HCID 131715086, compoundYield 116.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

In a manner similar to that of Example 1 (iii), 6-[4-(3-benzylaminopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (21.8 g) and 1-[4-(2-cyclopropylmethoxyethyl)phenoxy]-2,3-epoxypropane (19.4 g) in n-propanol (200 ml) were stirred under reflux for 41/2 hours. The mixture was cooled and a solution of fumaric acid (6.96 g) in hot n-propanol (150 ml) added with stirring. Cooling (and seeding) and stirring overnight afforded 6-[4-[3-[2-hydroxy-3-[4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-N-benzylpropylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone hemifumarate (31.05 g), m.p. 125°-8° C.

Workup

  1. temperatureunder reflux for 41/2 hours
  2. temperatureThe mixture was cooled
  3. temperatureCooling (and seeding)
  4. stirringstirring overnight

Sources & evidence

ORD record
ord-a12e83047d584aeab2d5a16ff2709d98
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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