Dimethylamine → HCID 44539633, compound

HRID 1616028Notes

Reaction equation

HRID 1616028 reaction equation
[Cl:1][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])[C:5](F)=[CH:4][CH:3]=1.[CH3:30][NH:31][CH3:32].CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][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])[C:5]([N:31]([CH3:32])[CH3:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 44540868HCID 44540868, compound

Product 1

HCID 44539633HCID 44539633, compoundYield 201.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

6-Chloro-3-fluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (188 mg, 0.46 mmol) was placed in a microwave vial and dissolved in THF (4 ml). Dimethylamine (0.463 ml, 0.93 mmol) and DIPEA (0.485 ml) were added and the mixture was heated at 160° C. for 1 h under microwave irradiation. The solvent was removed in vacuo and the yellow residue was dissolved in DCM (10 ml) and washed with water (10 ml). The DCM was removed in vacuo and the solid was dried in vacuo on a high vacuum line to afford the title compound (400 mg) as a yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe yellow residue was dissolved in DCM (10 ml)
  3. washwashed with water (10 ml)
  4. customThe DCM was removed in vacuo
  5. customthe solid was dried in vacuo on a high vacuum line

Sources & evidence

ORD record
ord-d746b15010074701a5bbe3ffd3df1833
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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