Acetic Acid → 6-[4-(2-t-butoxycarbonylaminopropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 1905423Notes

Reaction equation

C(OC([NH:11][C:12](C)([CH3:29])[CH2:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]([CH3:28])[CH2:23][C:24](=[O:27])[NH:25][N:26]=2)=[CH:17][CH:16]=1)=O)C1C=CC=CC=1.NC1C=[CH:36][C:35]([C:38]2C(C)CC(=O)NN=2)=[CH:34]C=1.C(=O)CC.C([BH3-])#N.[Na+].[C:54]([OH:57])(=[O:56])C>>[C:35]([O:57][C:54]([NH:11][CH:12]([CH3:29])[CH2:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]([CH3:28])[CH2:23][C:24](=[O:27])[NH:25][N:26]=2)=[CH:17][CH:16]=1)=[O:56])([CH3:38])([CH3:36])[CH3:34]

Participants

Reactant 5

HCID 176Acetic Acid

HCID 527Propanal

HCID 161928Ici 109,081

HCID 5003444Sodium cyanoborohydride

HCID 145786766-[4-(2-benzyloxycarbonylamino-2-methylpropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 145787126-[4-(2-t-butoxycarbonylaminopropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Procedure

The same operation as in Example 1, (1-c) was carried out by using 6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (2.03 g), 2-butoxycarbonylamino)propanal (2.09 g), acetic acid (0.6 g) and sodium cyanoborohydride (0.33 g), to obtain 6-[4-(2-t-butoxycarbonylaminopropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (2.89 g).

Sources & evidence

ORD record: ord-15d44fa856f8405fbe9f5b407896fa02
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04843072

Reaction notes

Loading…