Pyrrolidine → HCID 44540960, compound

HRID 1616018Notes

Reaction equation

HRID 1616018 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])[CH:5]=[CH:4][CH:3]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[NH:24]1[C:25]2[C:21](=[C:20]([C:18]3[CH:17]=[C:16]4[C:12]([CH:13]=[N:14][NH:15]4)=[C:11]([NH:10][C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[N:7]=4)=[O:9])[CH:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 44540963HCID 44540963, compound

Product 1

HCID 44540960HCID 44540960, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Conditions

Temperature
160 °C

Procedure

To a microwave vial was added 2 ml of a solution of 6-chloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (350 mg, 0.26 mmol, prepared as described in Example 18) in DMSO (14 ml). Pyrrolidine (0.022 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 160° C. for 3 h under microwave irradiation. The crude reaction mixture was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method B). Product-containing fractions were dried under a stream of nitrogen to afford the title compound (17.6 mg).

Workup

  1. customThe crude reaction mixture
  2. custompurified by Mass Directed Automated Preparative HPLC (Method B)
  3. customProduct-containing fractions were dried under a stream of nitrogen

Sources & evidence

ORD record
ord-0309e3c32948481aa75e2cac999a2b6a
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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