Ammonia → HCID 66604332, compound

HRID 2410848Notes

Reaction equation

HRID 2410848 reaction equation
C([C:3]1[O:7][C:6]([C:8]2[CH:9]=[C:10]([C:27]([NH2:29])=[O:28])[C:11]3[NH:12][C:13]4[CH:14]=[C:15]([N:21]5[CH2:26][CH2:25][O:24][CH2:23][CH2:22]5)[CH:16]=[CH:17][C:18]=4[C:19]=3[N:20]=2)=[CH:5][CH:4]=1)=O.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.[C:36](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(C(F)(F)F)=O.N>ClCCCl.CO.O>[O:24]1[CH2:25][CH2:26][N:21]([C:15]2[CH:16]=[CH:17][C:18]3[C:19]4[N:20]=[C:8]([C:6]5[O:7][C:3]([CH2:36][N:30]6[CH2:35][CH2:34][O:33][CH2:32][CH2:31]6)=[CH:4][CH:5]=5)[CH:9]=[C:10]([C:27]([NH2:29])=[O:28])[C:11]=4[NH:12][C:13]=3[CH:14]=2)[CH2:22][CH2:23]1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 6422Trifluoroacetic acid2×HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 86663062HCID 86663062, compound

Product 1

HCID 66604332HCID 66604332, compoundYield 72.7%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent3×HCID 962WaterSolvent2×

Procedure

A suspension of 2-(5-formylfuran-2-yl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (14 mg, 0.022 mmol), morpholine (19 uL, 0.22 mmol), and sodium triacetoxyborohydride (24 mg, 0.11 mmol) in 1,2-dichloroethane (0.3 mL) was stirred at RT overnight. 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 60% B over 10 min at 42 mL/min) followed by SCX capture and release with 2 N NH3 in MeOH gave 7-morpholino-2-(5-(morpholinomethyl)furan-2-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (7.8 mg, 0.016 mmol, 44% yield). MS (ESI) m/z 462.33 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.27 (1H, d, J=8.55 Hz), 7.98 (1H, s), 7.11 (1H, d, J=3.05 Hz), 6.98 (1H, dd, J=8.70, 1.98 Hz), 6.91 (1H, d, J=1.83 Hz), 6.42 (1H, d, J=3.36 Hz), 3.88-3.98 (4H, m), 3.75-3.84 (4H, m), 3.65 (2H, s), 3.29-3.38 (4H, m), 2.53-2.69 (4H, m).

Sources & evidence

ORD record
ord-43714b52a73443dcac99e25eb3e339ec
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…