Dimethylformamide → HCID 71280585, compound

HRID 1497896Notes

Reaction equation

HRID 1497896 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]([OH:15])=O)=[CH:11][N:12]=2)[CH:9]=1)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CN(C)C=O.[F:27][C:28]1([F:45])[CH2:31][CH:30]([C:32]2[O:36][N:35]=[C:34]([C:37]3[CH:38]=[CH:39][C:40]([CH3:44])=[C:41]([CH:43]=3)[NH2:42])[N:33]=2)[CH2:29]1>ClCCl.N1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]([NH:42][C:41]3[CH:43]=[C:37]([C:34]4[N:33]=[C:32]([CH:30]5[CH2:29][C:28]([F:45])([F:27])[CH2:31]5)[O:36][N:35]=4)[CH:38]=[CH:39][C:40]=3[CH3:44])=[O:15])=[CH:11][N:12]=2)[CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 71280746HCID 71280746, compoundHCID 86677525HCID 86677525, compound

Product 1

HCID 71280585HCID 71280585, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of 6-acetylimidazo[1,2-a]pyridine-3-carboxylic acid (24r) (71 mg, 0.39 mmol) in dichloromethane (2 mL) was added dropwise oxalyl chloride (173 uL, 1.98 mmol) and a drop of anhydrous N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 30 minutes and concentrated. The residue was treated with 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) (85 mg, 0.29 mmol) in anhydrous pyridine (2 mL) with stirring at room temperature for 30 minutes. The crude product was purified on silica gel using 10% MeOH in dichloromethane to give 6-acetyl-N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (115). 1H NMR (400 MHz, d6-DMSO) δ 10.24 (s, 1H), 10.13 (s, 1H), 8.70 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.95 (dd, J=2.0, 9.6 Hz, 1H), 7.88-7.84 (m, 2H), 7.52 (d, J=8.4 Hz, 1H), 3.92-3.84 (m, 1H), 3.24-3.02 (m, 4H), 2.64 (s, 3H), 2.38 (s, 3H). MS m/z 433.16 (M+1)+.

Workup

  1. concentrationconcentrated
  2. stirringwith stirring at room temperature for 30 minutes
  3. customThe crude product was purified on silica gel using 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-b3a7697bf2c5442eb000142ddbf6de4b
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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