HCID 14003355, compound → HCID 70429469, compound

HRID 1906667Notes

Reaction equation

HRID 1906667 reaction equation
C([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.[CH2:28]([C:31]1[CH:41]=[C:40]([CH2:42][CH2:43][O:44][CH2:45][CH:46]2[CH2:48][CH2:47]2)[CH:39]=[CH:38][C:32]=1[O:33][CH2:34][CH:35]1[O:37][CH2:36]1)[CH:29]=[CH2:30]>C(O)CC>[OH:37][CH:35]([CH:34]([CH2:20][C:17]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1)[O:33][C:32]1[CH:38]=[CH:39][C:40]([CH2:42][CH2:43][O:44][CH2:45][CH:46]2[CH2:48][CH2:47]2)=[CH:41][C:31]=1[CH2:28][CH:29]=[CH2:30])[CH2:36][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

4

Reactant 2

HCID 14003355HCID 14003355, compoundHCID 20211966HCID 20211966, compound

Product 1

HCID 70429469HCID 70429469, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 6-[4-(3-benzylaminopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (5.5 g; 0.015 mol), 1-[2-allyl-4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2,3-epoxypropane (8.65 g; 0.03 mol) and n-propanol (100 ml) was stirred under reflux for 24 hours. The mixture was cooled, filtered and the filtrate was evaporated under reduced pressure and chromatographed on a silica gel column, using ethyl acetate as eluant, to give as a glass 6-[4-[3-[2-hydroxy-3-[2-allyl-4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-N-benzylpropylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (4.4 g).

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated under reduced pressure
  5. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-9d3afdf02c27490dabe592322dea815a
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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