1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Tert-butyl 5-(6-(1-phenylcyclopropyl)-2-thioxo-1,2-dihydropyridin-3-ylcarbamoyl)isoindoline-2-carboxylate
Reaction equation
[NH2:1][C:2]1[C:3](=[S:17])[NH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[C:18]([O:22][C:23]([N:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:34](O)=[O:35])[CH:31]=2)[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].O.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CO.CN(C=O)C>[C:11]1([C:8]2([C:5]3[NH:4][C:3](=[S:17])[C:2]([NH:1][C:34]([C:30]4[CH:31]=[C:32]5[C:27](=[CH:28][CH:29]=4)[CH2:26][N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH2:33]5)=[O:35])=[CH:7][CH:6]=3)[CH2:10][CH2:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione (106 mg, 0.437 mmol) was added 2-(tert-butoxycarbonyl)isoindoline-5-carboxylic acid (115 mg, 0.437 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (67.0 mg, 0.437 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (84 mg, 0.437 mmol), and DMF (437 μL) before it was stirred at ambient T for 16 h. The reaction mixture was diluted with methanol before it was passed through a cartridge of cation exchange resinto give tert-butyl 5-(6-(1-phenylcyclopropyl)-2-thioxo-1,2-dihydropyridin-3-ylcarbamoyl)isoindoline-2-carboxylate after concentration. MS (ESI) m/z: Calculated: 487.2; Observed: 488.4 (M++H).
Sources & evidence
- ORD record
- ord-1ab39316e3f1455e8ef2568cb3d0ecb2
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842685B2
Reaction notes
Loading…