1-Propanol → HCID 70429640, compound

HRID 1906670Notes

Reaction equation

HRID 1906670 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.[CH3:28][C:29]1[CH:39]=[C:38]([CH2:40][CH2:41][O:42][CH2:43][CH:44]2[CH2:46][CH2:45]2)[CH:37]=[CH:36][C:30]=1[O:31][CH2:32][CH:33]1O[CH2:34]1.ClCCl.[C:50](#N)[CH3:51].[CH3:53][OH:54].[CH2:55](O)[CH2:56][CH3:57]>>[OH:54][CH:53]([CH:32]([CH2:33][C:34]1[CH:51]=[CH:50][CH:57]=[CH:56][CH:55]=1)[O:31][C:30]1[CH:36]=[CH:37][C:38]([CH2:40][CH2:41][O:42][CH2:43][CH:44]2[CH2:46][CH2:45]2)=[CH:39][C:29]=1[CH3:28])[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]

Participants

5

Reactant 4

HCID 10311-PropanolHCID 14003355HCID 14003355, compoundHCID 20211976HCID 20211976, compoundHCID 22226298MeOH ACN DCM

Product 1

HCID 70429640HCID 70429640, compound

Procedure

6-[4-(3-Benzylaminopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (7.0 g; 0.019 mol) and 1-[2-methyl-4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2,3-epoxypropane (7.32 g; 0.028 mol) were stirred under reflux in n-propanol (200 ml) for 17 hours. n-Propanol (100 ml) was distilled off and the mixture subjected to reflux for a further 24 hours. The reaction mixture was cooled, filtered and evaporated under reduced pressure to give an oily residue. This was subjected to high pressure liquid chromatography with dichloromethane:acetonitrile:methanol (200:4:4) as eluant. The fractions containing the desired compound were collected and evaporated under reduced pressure to give 6-[4-[3-[2-hydroxy-3-[2-methyl-4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-N-benzylpropylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (5.2 g) as an oil. Unreacted epoxide (3.6 g) was also recovered.

Workup

  1. distillationn-Propanol (100 ml) was distilled off
  2. temperatureto reflux for a further 24 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give an oily residue

Sources & evidence

ORD record
ord-1680e5ed764748a1be6125f0b5efc56c
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

Loading…