Dimethylformamide → HCID 71280491, compound

HRID 1497924Notes

Reaction equation

HRID 1497924 reaction equation
[O:1]=[C:2]([CH3:17])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([OH:16])=O)=[CH:12][N:13]=2)[CH:10]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[F:29][C:30]1([F:47])[CH2:33][CH:32]([C:34]2[O:38][N:37]=[C:36]([C:39]3[CH:40]=[CH:41][C:42]([CH3:46])=[C:43]([CH:45]=3)[NH2:44])[N:35]=2)[CH2:31]1>ClCCl.N1C=CC=CC=1>[F:47][C:30]1([F:29])[CH2:31][CH:32]([C:34]2[O:38][N:37]=[C:36]([C:39]3[CH:40]=[CH:41][C:42]([CH3:46])=[C:43]([NH:44][C:14]([C:11]4[N:9]5[CH:10]=[C:5]([CH2:4][CH2:3][C:2](=[O:1])[CH3:17])[CH:6]=[CH:7][C:8]5=[N:13][CH:12]=4)=[O:16])[CH:45]=3)[N:35]=2)[CH2:33]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 71280499HCID 71280499, compoundHCID 86677525HCID 86677525, compound

Product 1

HCID 71280491HCID 71280491, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of 6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxylic acid (78) (150 mg, 0.646 mmol) in anhydrous dichloromethane (5 mL) at 0° C. under Argon was added dropwise oxalyl chloride (60 μL, 0.710 mmol). Then, a drop of anhydrous N,N-dimethylformamide was added and the reaction mixture was stirred at room temperature for 45 minutes. The solvent was concentrated. A stirring mixture of the acid chloride and 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) (86 mg, 0.323 mmol) in anhydrous pyridine (3 mL) was stirred at room temperature for 3 hours. The crude product was purified by silica chromatography to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxamide (F53). 1H NMR (400 MHz, d6-DMSO) δ 10.19 (s, 1H), 9.37 (s, 1H), 8.70 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.86-7.83 (m, 2H), 7.66 (dd, J=1.6, 9.2 Hz, 1H), 7.51 (d, J=8.0 Hz, 1H), 3.92-3.84 (m, 1H), 3.24-3.05 (m, 4H), 2.89-2.86 (m, 4H), 2.37 (s, 3H), 2.11 (s, 3H). MS m/z 480.18 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated
  2. stirringwas stirred at room temperature for 3 hours
  3. customThe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-ebda8f03ad8742e8a4b2bf66f60a27d4
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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