1-Methylpiperazine → 2-(4-methylpiperazin-1-yl)-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamid

HRID 2410880Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CN1C(=O)CCC1>[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:2]2[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]3[NH:6][C:7]4[CH:8]=[C:9]([C:15]([N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)=[O:16])[CH:10]=[CH:11][C:12]=4[C:13]=3[N:14]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 180 °C

Procedure

A 0.5 ml microwave vial was loaded with 2-bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide (8 mg, 0.019 mmol), 1-Methylpiperazine (0.25 ml, 2.246 mmol) and NMP (0.25 ml), sealed and heated to 180° C. for 2 hours. Purification by prep HPLC, followed by filtration of the product containing fractions through gave a Waters MCX cartridge, washing with MeOH and elution with 2M NH3 in MeOH and drying gave 6.3 mg 2-(4-methylpiperazin-1-yl)-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamid. MS (ESI) m/e+=423, m/e−=421 consistent with [M+H]+ and [M−H]−. HPLC retention time 5.42 min. (Sunfire C18 3.5 μm, 4.6×150 mm column, 15 min gradient, 10-100% B, 1 mL/min. Solvent A: 5% CH3CN—95% H2O—0.1% TFA; Solvent B: 95% CH3CN—5% H2O—0.1% TFA). 1H NMR (CD3OD) δ ppm 8.25 (d, 1H, J=8.3), 7.67 (b, 1H), 7.42 (s, 1H), 7.26 (dd, 1H, J=8.0, 1.2), 3.90-3.50 (m, 12H), 2.74-2.66 (m, 4H), 2.41 (s, 3H).

Workup

customsealed
customPurification by prep HPLC
filtrationfollowed by filtration of the product
additioncontaining fractions
customthrough gave a Waters MCX cartridge
washwashing with MeOH and elution with 2M NH3 in MeOH
customdrying

Sources & evidence

ORD record: ord-b287789f533f41a59ccf0cca52043da8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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