Divinyl sulfone → HCID 66604190, compound

HRID 2410831Notes

Reaction equation

HRID 2410831 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21][N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)=[CH:17][CH:16]=4)[CH:12]=[C:11]([C:28]([NH2:30])=[O:29])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[CH:31]([S:33]([CH:36]=[CH2:37])(=[O:35])=[O:34])=[CH2:32]>CC(O)C>[O:34]=[S:33]1(=[O:35])[CH2:36][CH2:37][N:1]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:14]=[C:13]([C:15]5[CH:16]=[CH:17][C:18]([CH2:21][N:22]6[CH2:23][CH2:24][O:25][CH2:26][CH2:27]6)=[CH:19][CH:20]=5)[CH:12]=[C:11]([C:28]([NH2:30])=[O:29])[C:7]=4[NH:8][C:9]=3[CH:10]=2)[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 6496Divinyl sulfoneHCID 66604891HCID 66604891, compound

Product 1

HCID 66604190HCID 66604190, compoundYield 8.81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-amino-2-(4-(morpholinomethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (50 mg, 0.125 mmol), vinyl sulfone (0.13 mL, 1 3 mmol) in 2-propanol (3 mL) was stirred at 100° C. overnight. The solvent was removed and 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, 10-60% B at 42 mL/min over 20 min) followed by SCX capture and release with 2 N NH3 in MeOH afforded 7-(1,1-dioxido-4-thiomorpholinyl)-2-(4-(4-morpholinylmethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (6 mg, 10.97 μmol, 8.81% yield). MS (ESI) m/z 520.22 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.22 (1H, s), 8.54 (1H, br. s.), 8.30 (1H, s), 8.22 (2H, d, J=8.24 Hz), 8.09 (1H, d, J=8.55 Hz), 7.82 (1H,s),7.46 (2H, d, J=7.93 Hz), 7.32 (1H, d, J=2.14 Hz), 7.07 (1H, dd, J=8.85, 2.14 Hz), 3.88 (4H, br. s.), 3.58-3.65 (4H, m), 3.55 (2H, s), 3.20-3.27 (4H, m), 2.41 (4H, br. s.).

Workup

  1. customThe solvent was removed
  2. custompreparative 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, 10-60% B at 42 mL/min over 20 min)

Sources & evidence

ORD record
ord-688e58f2f88045e48d39c5843b00f254
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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