Diisopropylethylamine → 4-chloro-N-(5-(4((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamido)-2-methylphenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

HRID 709313Notes

Reaction equation

HRID 709313 reaction equation
[Cl:1][C:2]1[C:7]([C:8](O)=[O:9])=[CH:6][N:5]=[C:4]2[N:11]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:13][C:3]=12.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:57][C:58]1[CH:59]=[C:60]([NH:65][C:66](=[O:86])[C:67]2[CH:72]=[CH:71][C:70]([CH2:73][N:74]3[CH2:79][CH2:78][N:77]([CH2:80][CH3:81])[CH2:76][CH2:75]3)=[C:69]([C:82]([F:85])([F:84])[F:83])[CH:68]=2)[CH:61]=[CH:62][C:63]=1[CH3:64]>CN(C=O)C.O>[Cl:1][C:2]1[C:7]([C:8]([NH:57][C:58]2[CH:59]=[C:60]([NH:65][C:66](=[O:86])[C:67]3[CH:72]=[CH:71][C:70]([CH2:73][N:74]4[CH2:79][CH2:78][N:77]([CH2:80][CH3:81])[CH2:76][CH2:75]4)=[C:69]([C:82]([F:85])([F:84])[F:83])[CH:68]=3)[CH:61]=[CH:62][C:63]=2[CH3:64])=[O:9])=[CH:6][N:5]=[C:4]2[N:11]([S:14]([C:17]3[CH:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=3)(=[O:15])=[O:16])[CH:12]=[CH:13][C:3]=12

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67324831N-(3-amino-4-methylphenyl)-4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamideHCID 673458404-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 683056534-chloro-N-(5-(4((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamido)-2-methylphenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamideYield 78.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (50 mg, 0.14 mmol) in DMF (1 mL) were added HATU (162 mg, 0.43 mmol), DIEA (0.12 mL, 0.71 mmol) and N-(3-amino-4-methylphenyl)-4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide (60 mg, 0.14 mmol). The reaction mixture was stirred for overnight at room temperature after which, it was poured to water and the produced solid was filtered. The crude solid was dried with nitrogen gas flow. The title compound (85 mg, 0.11 mmol) was used next reaction without further purification. MS m/z: 753 [M+1].

Workup

  1. filtrationthe produced solid was filtered
  2. customThe crude solid was dried with nitrogen gas flow

Sources & evidence

ORD record
ord-70259937e1954cdc8b36caa4910071d8
Source dataset
uspto-grants-2015_11
Patent number
US09180127B2

Reaction notes

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