Diisopropylethylamine → N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 1497935Notes

Reaction equation

HRID 1497935 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([C:19]([O:21]CC)=O)=[CH:17][N:18]=3)[CH:15]=2)[CH2:4][CH2:3]1.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.C[NH:58][C:59]1[CH:64]=[C:63]([C:65]2[N:69]=[C:68]([CH:70]3[CH2:73][C:72]([F:75])([F:74])[CH2:71]3)[O:67][N:66]=2)[CH:62]=[CH:61][C:60]=1[CH3:76]>CN1C(=O)CCC1>[F:75][C:72]1([F:74])[CH2:71][CH:70]([C:68]2[O:67][N:66]=[C:65]([C:63]3[CH:62]=[CH:61][C:60]([CH3:76])=[C:59]([NH:58][C:19]([C:16]4[N:14]5[CH:15]=[C:10]([CH2:9][CH2:8][N:5]6[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]6)[CH:11]=[CH:12][C:13]5=[N:18][CH:17]=4)=[O:21])[CH:64]=3)[N:69]=2)[CH2:73]1

Participants

6

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 71280802Ethyl 6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxylateHCID 71280889Methyl 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline

Product 1

HCID 71280732N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirring solution of ethyl 6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxylate (114) (25 mg, 0.087 mmol) in anhydrous NMP (1 mL) was added HATU (26 mg, 0.104 mmol) and DIEA (23 uL, 0.130 mmol). The reaction mixture was stirred at room temperature for 10 minutes. Then, 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) (23 mg, 0.087 mmol) was added and the reaction was stirred for two days. The crude product was purified by reverse phase preparative HPLC to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxamide (F63). MS m/z 536.3 (M+1)+.

Workup

  1. stirringthe reaction was stirred for two days
  2. customThe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-6734a5b18bd14cfe9ddbfb3eae73ae37
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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