Ammonia → HCID 66605767, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:28]([NH2:30])=[O:29])[C:12]3[NH:13][C:14]4[CH:15]=[C:16]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)[CH:17]=[CH:18][C:19]=4[C:20]=3[N:21]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:32][CH2:33][Cl:34].C([O-])([O-])=O.[K+].[K+].C(O)(C(F)(F)F)=O.N>CN(C=O)C.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:28]([NH2:30])=[O:29])[C:12]3[NH:13][C:14]4[CH:15]=[C:16]([N:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)[CH:17]=[CH:18][C:19]=4[C:20]=3[N:21]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:32][CH2:33][Cl:34]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 40 °C
Procedure
A mixture of 2-(3-chloro-4-hydroxyphenyl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (120 mg, 0.284 mmol), 1-bromo-2-chloroethane (67 μL, 1.42 mmol) and K2CO3 (196 mg, 1.42 mmol) in DMF (4.8 mL) in a vial was heated at 40° C. for 3 h. Preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA; gradient of 0 to 100% B over 10 min at 42 mL/min) followed by SCX capture and release with 2 N NH3 in MeOH left 2-(3-chloro-4-(2-chloroethoxy)phenyl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (94 mg, 0.19 mmol, 68% yield) as a yellow solid. MS (ESI) m/z 485.22 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.25 (1H, s), 8.53 (1H, s), 8.36 (1H, d, J=2.44 Hz), 8.28 (1H, s), 8.23 (1H, dd, J=8.70, 2.29 Hz), 8.08 (1H, d, J=8.55 Hz), 7.83 (1H, s), 7.34 (1H, d, J=8.85 Hz), 7.22 (1H, d, J=2.14 Hz), 7.01 (1H, dd, J=8.85, 2.14 Hz), 4.43-4.48 (2H, m), 4.01-4.05 (2H, m), 3.78-3.84 (4H, m), 3.21-3.27 (4H, m).
Sources & evidence
- ORD record
- ord-68c91e09740b46c2821eceafacf18dfa
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815840B2
Reaction notes
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