Methanol → (E)-N-(2-Amino-5-(thiophen-2-yl)phenyl)-4-(3-(hydroxyamino)-3-oxoprop-1-enyl)benzamide

HRID 1907732Notes

Reaction equation

HRID 1907732 reaction equation
Cl.[OH:2][NH2:3].CN(C)[C@@H]1CCN(CC2C=CC(C(O)=O)=CC=2)C1.FC(F)(F)C(O)=O.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)=[CH:32][C:31]=1[NH:41][C:42]([C:44]1[CH:49]=[CH:48][C:47](/[CH:50]=[CH:51]/[C:52](O)=[O:53])=[CH:46][CH:45]=1)=[O:43].CO>C(Cl)Cl>[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)=[CH:32][C:31]=1[NH:41][C:42](=[O:43])[C:44]1[CH:45]=[CH:46][C:47](/[CH:50]=[CH:51]/[C:52]([NH:3][OH:2])=[O:53])=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 59737509(R)-4-((3-(Dimethylamino)pyrrolidin-1-yl)methyl)benzoic acidHCID 69101378(E)-3-(4-(2-Amino-5-(thiophen-2-yl)phenylcarbamoyl)phenyl)acrylic acid trifluoroacetate

Product 1

HCID 59737322(E)-N-(2-Amino-5-(thiophen-2-yl)phenyl)-4-(3-(hydroxyamino)-3-oxoprop-1-enyl)benzamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the same procedure as described in Example 1, step 6 (scheme 1), but substituting compound 4 for N-hydroxylamine hydrochloride salt and compound 7 for compound 226, the title compound 227 was obtained as a yellowish solid in 79% yield [purified by flash chromatography (eluent: 5% to 66% MeOH in DCM)].

Sources & evidence

ORD record
ord-b7bf7214934c4f8d852c225abd04e7b9
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

Loading…