Dimethylamine → HCID 44540870, compound

HRID 1616019Notes

Reaction equation

HRID 1616019 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.[CH3:29][NH:30][CH3:31].CCN(C(C)C)C(C)C>CS(C)=O>[CH3:29][N:30]([CH3:31])[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

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 81531DiisopropylethylamineHCID 44540963HCID 44540963, compound

Product 1

HCID 44540870HCID 44540870, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 6-chloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (40 mg, 0.10 mmol, prepared as described in Example 18) in DMSO (1 ml) was added dimethylamine (2M in THF, 0.052 ml, 0.10 mmol) and DIPEA (0.09 ml). The mixture was heated under microwave irradiation firstly at 140° C. for 1 h, then at 160° C. for 1 h and then at 180° C. for 1 h. Further dimethylamine (2M in THF, 0.052 ml, 0.10 mmol) was added and the mixture was heated under microwave irradiation at 160° C. for 2 h. The product was then purified by Mass Directed Automated Preparative HPLC (Method B), then further purified by chromatography using an SCX cartridge (1 g), which was eluted with MeOH (2 column volumes) and then ammonia in MeOH (2M, 1 column volume). The product-containing fractions were combined and blown down under a stream of nitrogen. Purification using an aminopropyl cartridge (1 g), which was eluted with MeOH (1 column volume), afforded the title compound (9.8 mg) as a pale orange gum.

Workup

  1. waitat 180° C. for 1 h
  2. temperaturethe mixture was heated under microwave irradiation at 160° C. for 2 h
  3. customThe product was then purified by Mass Directed Automated Preparative HPLC (Method B)
  4. customfurther purified by chromatography
  5. washwas eluted with MeOH (2 column volumes)
  6. customPurification
  7. washwas eluted with MeOH (1 column volume)

Sources & evidence

ORD record
ord-341e55a739d648b287df163545166d57
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

Loading…