3-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluorobenzoic acid → (S)-7-Bromo-N-(5-((5,5-dimethyltetrahydrofuran-2-yl)methylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335342

Reaction equation

HRID 335342 reaction equation
[Cl-].[CH3:2][C:3]1([CH3:10])[O:7][C@@H:6]([CH2:8][NH3+:9])[CH2:5][CH2:4]1.[Br:11][C:12]1[CH:17]=[CH:16][N:15]2[C:18]([C:21]([NH:23][C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=3[F:33])[C:27](O)=[O:28])=[O:22])=[CH:19][N:20]=[C:14]2[CH:13]=1>>[Br:11][C:12]1[CH:17]=[CH:16][N:15]2[C:18]([C:21]([NH:23][C:24]3[CH:25]=[C:26]([C:27](=[O:28])[NH:9][CH2:8][C@@H:6]4[CH2:5][CH2:4][C:3]([CH3:10])([CH3:2])[O:7]4)[CH:30]=[CH:31][C:32]=3[F:33])=[O:22])=[CH:19][N:20]=[C:14]2[CH:13]=1

Participants

3

Reactant 2

HCID 712834433-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluorobenzoic acid2×HCID 86695690(R)-(5,5-dimethyltetrahydrofuran-2-yl)methanaminium chloride2×

Product 1

HCID 71282935(S)-7-Bromo-N-(5-((5,5-dimethyltetrahydrofuran-2-yl)methylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

Procedure

The title compound was prepared from (R)-(5,5-dimethyltetrahydrofuran-2-yl)methanaminium chloride (Intermediate 9B) and 3-(7-Bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-fluoro benzoic acid (prepared by hydrolysis of methyl 3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-fluorobenzoate (Intermediate 1A) using NaOH) analogously to Example 7.4 step 1;

Sources & evidence

ORD record
ord-fe25fa673bbe401ca95296ba172be2a0
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Linked notes

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