Diisopropylamine → Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:39])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:36](O)=[O:37])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+:41].C(NC(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O.O>[C:36]([C:21]1[C:22]2[NH:23][C:24]3[C:29]([C:30]=2[C:18]([C:14]2[C:13]([CH3:39])=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:17]=[CH:16][CH:15]=2)=[CH:19][N:20]=1)=[CH:28][CH:27]=[C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])[CH:25]=3)(=[O:37])[NH2:41]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.237 g, 0.451 mmol), ammonium chloride (0.096 g, 1.804 mmol), N,N-diisopropylamine (0.378 mL, 2.165 mmol), BOP (0.259 g, 0.586 mmol), and N-methylmorpholine (0.193 mL, 1.759 mmol) in N,N-dimethylformamide (3 mL) was stirred at room temperature for 1.5 hr. To the reaction mixture was added water (30 mL), and the resulting mixture was stirred at room temperature for 30 min. The insoluble product (0.226 g, 0.431 mmol, 96% yield) was collected as a beige solid by suction filtration and dried over Drierite under vacuum.
Workup
- stirringthe resulting mixture was stirred at room temperature for 30 min
Sources & evidence
- ORD record
- ord-ccfb4061749e4cbea820efcbdda23ed2
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685969B2
Reaction notes
Loading…