Dimethylformamide → HCID 71281511, compound

HRID 570362Notes

Reaction equation

HRID 570362 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]([OH:14])=O)=[CH:10][N:11]=[C:5]2[CH:4]=1.CN(C=O)C.[NH2:22][C:23]1[CH:24]=[C:25]([C:30]2[N:34]=[C:33]([CH:35]3[CH2:38][N:37]([C:39]([O:41][CH3:42])=[O:40])[CH2:36]3)[O:32][N:31]=2)[CH:26]=[CH:27][C:28]=1[CH3:29]>ClCCl.N1C=CC=CC=1>[CH3:29][C:28]1[CH:27]=[CH:26][C:25]([C:30]2[N:34]=[C:33]([CH:35]3[CH2:36][N:37]([C:39]([O:41][CH3:42])=[O:40])[CH2:38]3)[O:32][N:31]=2)=[CH:24][C:23]=1[NH:22][C:12]([C:9]1[N:6]2[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:16])[F:15])=[CH:4][C:5]2=[N:11][CH:10]=1)=[O:14]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 712804827-(Trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 86677444Methyl 3-(3-(3-amino-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate

Product 1

HCID 71281511HCID 71281511, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring suspension of 7-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (24) (89 mg, 0.387 mmol) in anhydrous dichloromethane (3 mL) at 0° C. under Argon oxalyl chloride (34 uL, 0.407 mmol) was added dropwise. Then, a drop of anhydrous DMF was added and the reaction mixture was stirred at 0° C. for 1.5 hours. The solvent was concentrated and the crude solid was added to a stirring solution of methyl 3-(3-(3-amino-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (31) (19 mg, 0.0645 mmol) in anhydrous pyridine (1.5 mL) at 0° C. The reaction was stirred at room temperature under Argon for 20 minutes. The crude product was filtered and purified by preparative HPLC to give methyl 3-(3-(4-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxamido)phenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (F57). 1H NMR (400 MHz, d6-DMSO) δ 10.25 (s, 1H), 9.64-9.61 (m, 1H), 9.75 (s, 1H), 8.33-8.30 (m, 1H), 8.10 (dd, J=1.6 Hz, 1H), 7.86 (dd, J=1.6, 8.0 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.46 (dd, J=2.0, 7.6 Hz, 1H), 4.40-4.33 (m, 2H), 4.31-4.25 (m, 1H), 4.22-4.18 (m, 2H), 3.59 (s, 3H), 2.38 (s, 3H). MS m/z 501.43 (M+1)+.

Workup

  1. additionwas added dropwise
  2. concentrationThe solvent was concentrated
  3. stirringThe reaction was stirred at room temperature under Argon for 20 minutes
  4. filtrationThe crude product was filtered
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-1366fb79e6fe495494cbf08906a07035
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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