Potassium Carbonate → HCID 66580801, compound

HRID 1521874Notes

Reaction equation

HRID 1521874 reaction equation
[N:1]1([C:7]([C:9]2[C:10]3[CH2:29][S:28](=[O:31])(=[O:30])[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:11]=3[N:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[C:17]#[N:18])[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:32]([N:35]=[N+:36]=[N-])(=O)[CH3:33].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH3:33][C:32]1[NH:35][N:36]=[C:17]([C:16]2[CH:15]=[C:14]([N:12]3[C:11]4[C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=5[S:28](=[O:30])(=[O:31])[CH2:29][C:10]=4[C:9]([C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:8])=[N:13]3)[CH:21]=[CH:20][CH:19]=2)[N:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12841679Acetyl azideHCID 68228419HCID 68228419, compound

Product 1

HCID 66580801HCID 66580801, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-[3-(morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]benzonitrile (100 mg, 0.23 mmol) in dry toluene is added acetic azide (34 mg, 0.46 mmol) and K2CO3 (158 mg, 0.115 mmol) under nitrogen. The reaction mixture is heated to 110° C. for 12 h under nitrogen after which it is concentrated under vacuum. The solid residue is purified by Preparative HPLC to afford the title compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.21-8.19 (d, J=7.7 Hz, 1H), 8.03-7.98 (m, 2H), 7.73-7.69 (m, 1H), 7.64-7.56 (m, 3H), 6.92-6.90 (d, J=7.8 Hz, 1H), 4.91 (s, 2H), 3.93 (m, 2H),3.75-3.67 (m, 4H), 3.62-3.61 (m, 2H), 2.37 (s, 3H). MS (ESI+): 491.0. HPLC (max plot) 98.76%; Rt 2.96 min.

Workup

  1. concentrationis concentrated under vacuum
  2. customThe solid residue is purified by Preparative HPLC

Sources & evidence

ORD record
ord-d83ebb1b0f034a5c925744e344cacea5
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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