Ammonia → HCID 66605029, compound

HRID 2410771Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:31]([O:33]C)=O)[C:11]3[NH:12][C:13]4[CH:14]=[C:15]([O:21][CH2:22][CH2:23][CH2:24][N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[CH:16]=[CH:17][C:18]=4[C:19]=3[N:20]=2)=[CH:4][CH:3]=1.[NH3:35]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:31]([NH2:35])=[O:33])[C:11]3[NH:12][C:13]4[CH:14]=[C:15]([O:21][CH2:22][CH2:23][CH2:24][N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[CH:16]=[CH:17][C:18]=4[C:19]=3[N:20]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of crude methyl 2-(4-chlorophenyl)-7-(3-morpholinopropoxy)-5H-pyrido[3,2-b]indole-4-carboxylate (75 mg, 0.16 mmol) in 7 N NH3 in MeOH (4 mL) in a sealed microwave vial was heated at 80° C. overnight. The product was isolated by preparative HPLC (100×30 mm Luna C18 column, gradient elution with A:B=30:70 to A:B=0:100 [A=10 mM NH4OAc in 5% aq. CH3CN; B=10 mM NH4OAc in 95% aq. CH3CN] over 20 min) followed by removal of the solvents on the SPEEDVAC® to leave 2-(4-chlorophenyl)-7-(3-morpholinopropoxy)-5H-pyrido[3,2-b]indole-4-carboxamide (34.6 mg, 0.071 mmol, 45% yield) as a yellow solid. MS (ESI) m/z 465.0 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.45 (1H, s), 8.57 (1H, s), 8.37 (1H, s), 8.28-8.33 (2H, m), 8.11 (1H, d, J=8.56 Hz), 7.87 (1H, s), 7.54-7.63 (2H, m), 7.28 (1H, d, J=2.27 Hz), 6.88 (1H, dd, J=8.69, 2.14 Hz), 4.11 (2H, t, J=6.29 Hz), 3.59 (4H, br. s.), 2.45 (2H, br. s.), 2.32-2.45 (4H, m), 1.96 (2H, br. s.).

Workup

customThe product was isolated by preparative HPLC (
wash100×30 mm Luna C18 column, gradient elution with A:B=30:70 to A:B=0:100 [A=10 mM NH4OAc in 5% aq. CH3CN
customB=10 mM NH4OAc in 95% aq. CH3CN] over 20 min) followed by removal of the solvents on the SPEEDVAC®

Sources & evidence

ORD record: ord-fe75dce2479346a9962d9ffb076d1cef
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

Loading…