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Dimethylformamide → Labuxtinib

HRID 1497943
Notes
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Reaction equation

HRID 1497943 reaction equation
[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[F:24][C@@H:25]1[CH2:27][C@H:26]1[C:28]1[O:32][N:31]=[C:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:40])=[C:37]([CH:39]=2)[NH2:38])[N:29]=1>ClCCl.N1C=CC=CC=1>[F:24][C@H:25]1[CH2:27][C@@H:26]1[C:28]1[O:32][N:31]=[C:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:40])=[C:37]([NH:38][C:10]([C:3]3[N:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]4=[N:1][CH:2]=3)=[O:12])[CH:39]=2)[N:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acidHCID 86677536HCID 86677536, compound

Product 1

HCID 71280305Labuxtinib

Reagents, catalysts & solvents 2

HCID 1049Pyridine
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (52 mg, 0.32 mmol) in anhydrous dichloromethane (2 mL) at 0° C. under Argon was added dropwise oxalyl chloride (56 μL, 0.64 mmol). Then, a drop of anhydrous DMF was added and the reaction mixture was stirred at room temperature for 1.5 hours. The solvent was concentrated and the crude solid was added portion-wise to a stirring solution of 5-(5-((1S,2R)-2-fluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (132) (62 mg, 0.27 mmol) in anhydrous pyridine (1 mL) at 0° C. The reaction was stirred at room temperature under Argon for 30 minutes and quenched with water. The crude product was purified by preparative HPLC to yield N-(5-(5-((1R,2S)-2-fluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F113). MS m/z 378.1 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated
  2. stirringThe reaction was stirred at room temperature under Argon for 30 minutes
  3. customquenched with water
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-63832990bce44e889dc25b8f784e4683
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199981B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes