4-[(Aminooxy)methyl]benzonitrile hydrochloride → HCID 44554360, compound
Reaction equation
O=C1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:26])[NH:17][CH2:18][CH2:19][O:20][C:21](=[O:25])[C:22]([CH3:24])=[CH2:23])[CH:10]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=2[C:4](=[O:31])O1.Cl.[C:33]([C:35]1[CH:43]=[CH:42][C:38]([CH2:39][O:40][NH2:41])=[CH:37][CH:36]=1)#[N:34]>>[C:33]([C:35]1[CH:43]=[CH:42][C:38]([CH2:39][O:40][NH:41][C:4]([C:5]2[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=2[NH:7][CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:26])[NH:17][CH2:18][CH2:19][O:20][C:21](=[O:25])[C:22]([CH3:24])=[CH2:23])[CH:10]=2)=[O:31])=[CH:37][CH:36]=1)#[N:34]Participants
Procedure
To a stirred solution of 1-(2-amino-pyridin-4-ylmethyl)-1H-benzo[d][1,3]oxazine-2,4-dione (1.2 g, see preparation 7b) in pyridine was added isocyanatoethyl methacrylate (0.76 ml). The reaction mixture was heated to 40° C. and stirred for 2 hours. More isocyanatoethyl methacrylate (0.1 ml) was added and stirring was continued for 2 hours. The solvent was evaporated under reduced pressure and EtOAc (10 ml) was added to the residue. On scraping a solid material formed, that was isolated by filtration and dried in vacuo, affording 2-methyl-acrylic acid 2-{3-[4-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-pyridin-2-yl]-ureido}-ethyl ester (1.78 g). Step 2: This anhydride intermediate was converted into the title compound by reaction with O-(4-cyanobenzyl)hydroxylamine hydrochloride (see preparation 10), using general procedure 1A. 13C-NMR (DMSO-d6) δ 167.5, 166.5, 154.8, 153.7, 151.4, 148.6, 146.6, 141.9, 135.8, 132.8, 132.3, 129.2, 128.1, 125.9, 118.8, 115.4, 114.9, 113.0, 111.6, 110.9, 109.4, 76.1, 63.7, 45.4, 38.0, 18.0.
Sources & evidence
- ORD record
- ord-f088b51b792d4f079b8904f86b378ae1
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08034811B2
Reaction notes
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